Celebrities

40+ of the Best and Worst Oscar Dresses of All Time

It’s red carpet season again, and we’re here for ALL the glitz and glam Hollywood brings! The Academy Awards, aka the Oscars, are the pinnacle of award season, so you’re guaranteed to see nominees and guests sporting all the bells and whistles that top designers can muster. But are all these dresses what they’re cracked up to be? Some are memorable in a good way, whereas others are not. Let’s see who made their mark on our scale of best and worst.

Louis Ferguson

An editor at Explore Factor

Jan 16, 2024
5 min read

Angelina Jolie – 2004

The brunette beauty wore a classic-looking satin halter dress designed by Marc Bouwer. While not over-the-top, its sultry subduedness made it stand out among the rest on that night. The creamy white of the satin shone against Angelina’s tan skin, and the whole look gave us Marilyn Monroe vibes.

Angelina Jolie – 2004

Some have declared this dress an Oscar winner, and it absolutely qualifies to be on this list! Angie definitely knows how to put her best look forward.

Audrey Hepburn – 1953

One of the world’s most adored actresses, Audrey Hepburn, never failed to make her mark wherever she went. Back in the early days of the Oscars, the ceremony wasn’t the pomp and ceremony it is today, and cocktail dresses were the norm. Audrey, winning Best Actress for Roman Holiday, looks positively stunning in this white Givenchy dress.

Audrey Hepburn – 1953

It’s no wonder she wore a Givenchy design, as she was great friends with Hubert de Givenchy. The unique boat neckline showed off Audrey’s slim neck and perfect posture, and that style wasn’t common for such an occasion. It’s no wonder it’s been a celebrated Oscar design since then.

Bjork – 2001

Well, what can we say here? It makes a statement, that’s for sure! The Icelandic singer was covered in feathery tulle and a swan’s neck draped around her neck, ending with its head strategically covering her chest. Not only did she wear this dress, but she, um, laid eggs walking down the red carpet!

Bjork – 2001

Although this dress was (and still is) certainly capturing negative attention at the time, we have to conclude that it’s become iconic all these decades later.

Catherine Zeta-Jones – 2003

No stranger to red carpets, this Welsh actress walked away with the Best Supporting Actress for her role in Chicago. At the time, Catherine was heavily pregnant with her daughter, Carys, but Versace came through for her and created a stunning gown in an unusual yet complimentary color.

Catherine Zeta-Jones – 2003

We can’t imagine being all dressed up and having to sit through an entire Oscar ceremony as it is, but being nine months pregnant as well?! At least the dress looked comfortable!

Charlize Theron – 2010

Charlize usually hits all the right notes when attending red-carpet events, yet she missed one here in 2010. The color of the gown is gorgeous, but what on Earth are those things on her chest?

Charlize Theron – 2010

They just call ALL the attention, don’t they?! The Dior spokeswoman just left us with gaping mouths. We all make mistakes, Charlize, so don’t feel too bad. At least this dress shows off her stunning figure.

Cher – 1974

Ah, Cher, always putting a toe over the line and making us gasp. While Cher has some memorable Oscar outfits, and there’s always another one coming up, this one makes us wonder what she was thinking. Didn’t she get the memo that the Academy Awards required formal attire, not beachwear?

Cher – 1974

While we commend Cher for being different, sometimes it can be too much. Then again, Cher likes that this part of her personality brings her attention – negative attention included.

Cindy Crawford – 1993

The supermodel looked heavenly in this white bandage dress from designer Herve Leger. It’s a simple style that showed off her model figure. Embellished with a simple updo and sparkly diamonds, Richard Gere’s date was stunning.

Cindy Crawford – 1993

She had everyone looking her way. Being in the fashion world, Cindy is sure to know the right outfit to wear to a red carpet event.

Elizabeth Hurley – 1995

What an absolutely stunning dress, so perfect for the Oscars! The Versace design is adorned with sparkle, so Elizabeth didn’t need to add much jewelry apart from a bracelet and some earrings.

Elizabeth Hurley – 1995

Even her matching purse was bedazzled! Elizabeth has an eye for couture and this one, although not her most iconic look, is one of her best looks ever!

Gwyneth Paltrow – 1991

Sometimes, simple is the best way to go. This simple, baby-pink Ralph Lauren design made sure the night’s Oscar winner went down in the memory books. Gwyneth paired the dress with an equally simple slicked-back hairstyle and choker.

Gwyneth Paltrow – 1991

Yes, most of us remember her tearful acceptance speech, but at least she looked adorable! Gwyneth has gone on to say she’s kept most of her Oscar dresses for her daughter one day. We’re sure Apple will pick this stunner!

Demi Moore – 1989

Who on Earth comes up with some of these designs? Oh, it was Demi herself. Well, this proves that some things should absolutely be left to professionals. Who in their right mind would wear cycling shorts to the Academy Awards? There we said it; Demi was clearly not in her right mind.

Demi Moore – 1989

And that lining on the skirt bit just reminds us of Grandma’s curtains. Demi, you’re a gorgeous woman! Go and have a cup of coffee with a designer and give them your ideas next time.

Halle Berry – 2002

This Ellie Saab creation wowed us then and still wows us now! Halle Berry went on to win Best Actress for her role in Monsters Ball, and what a dress to accept such a prestigious award in!

Halle Berry – 2002

From the color to the delicate strategic embroidery, this dress will always be on the best-dressed list. We wonder if she still has it in her closet.

Edy Williams – 2000

Edy Williams always broke the rules when it came to attire for the Academy Awards. Although this one wasn’t as revealing as the ones she’s worn in the past, it screams more figure skater than red carpet.

Edy Williams – 2000

You can’t fault her toned body, but this dress just doesn’t suit her. They do say you should dress your age, and although we don’t want to be ageist, we do think perhaps this dress was too young for her.

Hilary Swank – 2005

Hilary may have won the Oscar that night, but this dress just made the win all that much sweeter! As she was walking up to the red carpet, you would never have guessed the dress was backless until Hilary turned around. And what a back!

Hilary Swank – 2005

This dress was perfect for showing off the actress’ lithe figure. Guy Laroche designed an immaculate outfit for an incredibly talented actress. The color, the material, everything just works!

Faith Hill – 2001

Who doesn’t love rainbows? We love rainbows, especially after rain. But we love them in the sky, not so much on our bodies. The style of Faith’s dress is gorgeous and fits the stunning country singer well; we just don’t agree with the colors at all.

Faith Hill – 2001

Let’s keep the rainbows in the sky and your songs, Faith. We’re confident you’ll get it right next time.

Jennifer Lawrence – 2013

Who can forget the night when JLaw won Best Actress for Silver Linings Playbook? We know she can’t, and it’s because of this dress. The Dior Haute Couture dress got tangled up while she was walking up the steps, and she fell. Poor thing! But she handled it with all the grace and style that we know her for.

Jennifer Lawrence – 2013

Jennifer let the dress do all the talking on the red carpet, as she only paired it with a very delicate necklace, earrings, and subtle makeup. It’s a very simple princess dress that allowed her to be a well-deserving princess for the night.

Geena Davis – 1992

Geena was nominated for her role in the iconic Thelma and Louise. It’s a pity her dress wasn’t as iconic as her movie, though. This design by Ruth Meyers and Bill Hargate looks more like a frothy milkshake than a dress worthy of an Oscar nominee.

Geena Davis – 1992

At least Geena has legs that can be shown off. But what are those ruffles at the bottom of the dress? Fashion sure was different in the early ’90s!

Jennifer Lopez – 2003

Not everyone can pull off a mint green dress, but JLo certainly can! From the one-shouldered overlay to the intricate embroidery, everything about this Valentino dress is perfect.

Jennifer Lopez – 2003

Jennifer’s flawless skin just glows with this color. Elaborate earrings, a simple bangle, and subdued makeup all make this look an absolute classic.

Jennifer Hudson – 2007

While we applaud anyone wearing a dress with pockets, this dress just… well, failed. Oscar de la Renta, we’re declaring our disappointment. The color looks amazing on Jen, but the style just doesn’t fit well. And what on Earth is that jacket doing? It doesn’t work!

Jennifer Hudson – 2007

It was said afterward that Jen did have another dress in the pipeline but was coerced into wearing this sad creation. What an absolute pity. Hopefully, the backlash made the person rethink their stance on forcing people to wear something they don’t want to wear.

Jessica Chastain – 2013

Old-school Hollywood glamor is never a bad thing, and Jessica shines in this Armani Prive gown. The geometric patterns just enhance the already stunning shape of the dress and highlight Jessica’s slim figure.

Jessica Chastain – 2013

The gold color compliments Jessica’s porcelain skin, and the lack of jewelry isn’t missed as she didn’t need any more than what she had. Her simple hairstyle is a perfect addition to round off this gorgeous outfit.

Kate Hudson – 2001

We love us some Kate Hudson, just not in this hodge-podge of eras. The dress’s neckline/collar and the hairstyle both look Victorian, while the rest of the dress looks modern. And the color?

Kate Hudson – 2001

The color is too drab for gorgeous Kate and definitely too dull for the Oscars. While Kate has gone on to declare that she loves this dress and still has it in her closet, sadly, no one shares her opinion.

Julia Roberts – 2001

The Erin Brockovich star collected her statuette in a Valentino design that she chose the week of the award ceremony. Talk about cutting it close!

Julia Roberts – 2001

The black floor-length gown had cleverly designed white piping up the front which formed a Y into the straps. This dress has often been referred to as an iconic Oscar gown, and we agree! Valentino has stated that seeing his design on the big Oscar stage was one of his proudest moments.

Kim Basinger – 1990

Here we have another actress who thought she could have a go at designing. Kim, honey, you either have the talent or you don’t, and we’re here to ask you to please stick to what you’re good at – acting.

Kim Basinger – 1990

This outfit looks like it can’t make up its mind. Is it a suit? Or is it a dress? We just don’t know, and our confusion is distracting us from the awards.

Kristen Wiig – 2020

Um, we honestly don’t know what to say here. The only thing that comes to mind is a frilly sea slug. We’re truly looking for some positives about this dress and coming up empty. It’s just ghastly!

Kristen Wiig – 2020

Kristen is such a lovely woman, but this doesn’t do her any favors. Not only is the dress weird but why is she wearing black gloves with it? Everything about this outfit is just wrong!

Lady Gaga – 2019

Black has always been a staple for elegance, and this Alexander McQueen creation screams elegance. Although we’re not too sure what’s going on with the hips, at least Lady Gaga can strike a pose with them!

Lady Gaga – 2019

The whole outfit was a tribute to Audrey Hepburn’s Breakfast at Tiffany’s look, including the huge diamond around Gaga’s neck. The very same stone was worn by Audrey back when she did publicity photos for the movie.

Lupita Nyong’o – 2014

This ethereal dress was made for Lupita by Prada, and the color is absolutely breathtaking on the actress. This was her first Oscar ceremony, and she was nominated for her role in 12 Years a Slave.

Lupita Nyong’o – 2014

She chose the color because it reminded her of her home in Kenya. We’re sure it brought her luck because she went on to win the Best Supporting Actress statuette.

Linda Cardellini – 2019

Linda didn’t get the memo that shag carpets went out of style in the ’70s. This fluffy mess might be a pretty color, but it’s not a pretty dress for any event.

Linda Cardellini – 2019

You’re a talented actress, Linda, but be sure to get on board with a proper wardrobe stylist next time.

Michelle Williams – 2006

This is an unusual color to wear on the red carpet, but Oscar-winner Michelle slays in this gorgeous dress. Nominated for her role in Brokeback Mountain, Michelle wowed in this Vera Wang gown, which was a throwback to vintage Hollywood.

Michelle Williams – 2006

Coupled with a simple bun in her hair, red lips, and a tiny clutch, this outfit is sure to go down in history as one of the best Oscar looks.

Lizzie Gardiner – 1995

Yes, the Oscars are all about golden this and that, but credit cards? Hmmm, how very odd. Odd, but certainly memorable. Lizzie won an Oscar for costume design on the movie Priscilla, Queen of the Desert, but somehow didn’t get it right for the red carpet.

Lizzie Gardiner – 1995

Don’t get us wrong, this dress is unique. But how on Earth did she handle the evening in it? How did she sit? How did she go to the bathroom? Enquiring minds want to know!

Miley Cyrus – 2009

The Hannah Montana star walked the red carpet in this Zuhair Murad creation and received lots of praise. The layered scales on the skirt remind us of a mermaid, and the shell-like design on the belt with accompanying pearl seals the deal.

Miley Cyrus – 2009

Miley grew up before our eyes, and when we saw her in this absolute stunner of a dress, we knew we were old! What a stunning dress for such a stunning young lady!

Sally Kirkland – 2007

Again, we’re reminded that sometimes you’re supposed to dress your age. Unfortunately, Sally didn’t get that message. Whatever she was trying to wear here fell short. Are those supposed to be butterfly wings?

Sally Kirkland – 2007

Your guess is as good as ours! We’re all for letting it all hang out if you can flaunt it, but if you can’t, have some self-respect and cover it up.

Nicole Kidman – 1997

Statuesque Nicole looks ravishing in this John Galliano-designed Christian Dior gown. The color is flawless on her and it complements her skin tone perfectly. If you didn’t notice, the neckline was influenced by another dress on this list, namely Audrey Hepburn’s 1953 Oscar dress.

Nicole Kidman – 1997

Her ex-husband, Tom Cruise was up for an Oscar that night, but everyone’s attention was on his arm candy in this uniquely gorgeous dress.

Tyra Banks – 2000

Supermodels getting it wrong seems to happen a lot but, thankfully, not too often. Sadly, Tyra Banks banked too much on this lilac number and came up short.

Tyra Banks – 2000

The tulle skirt looks like an afterthought and doesn’t match the material used for the bodice. Not everyone is perfect, we get it, but we didn’t expect Tyra and designer Vera Wang to fail so badly.

Penelope Cruz – 2007

This Atelier Versace dress with a patterned bodice that opens into a flowing feathered skirt is outstanding! Penelope is glowing with colors that compliment her flawless skin.

Penelope Cruz – 2007

Rounding the look out with an elegant updo, simple earrings, and a bracelet, the Oscar nominee looks radiant on the red carpet.

Uma Thurman – 2004

Exactly what is going on with this outfit? There’s so much tulle! And is that an attempt at a waistcoat? Nothing seems to match, neither color nor style. If we’re not mistaken, Uma doesn’t look all that comfortable or confident in this dress either. We don’t blame her!

Uma Thurman – 2004

Even though Uma picked it up off the Christian Lacroix runway for the Oscars, we’re sure she’s sorry she did. Perhaps this is a case of trying too hard to be different.

Sandra Bullock – 2010

Sandra channeled the Oscar statue itself with this metallic silvery-gold dress with lace overlay. It proved to be her good luck charm as she won the coveted award that night for her role in The Blind Side.

Sandra Bullock – 2010

Pairing the dress with a delicate bracelet, matching clutch, simple earrings, and her lovely brunette locks down, Sandra was a winner on the fashion front too.

Whoopi Goldberg – 1993

This controversial comedian and talk show cohost didn’t seem to have a clue what to wear to the 65th Academy Awards. While the jumpsuit is rather flamboyant, it’s the eye-watering lime green lining of the skirt that has us cringing.

Whoopi Goldberg – 1993

There’s so much going on here that we just need to say that simple is always better. This outfit is just too much in every aspect.

Taraji P. Hensen – 2018

Ending off our list with a good one, Taraji is oozing glamor in this custom Vera Wang creation. With the keyhole neckline and alluring yet understated slit, Taraji is radiant at the 90th Academy Awards.

Taraji P. Hensen – 2018

This just goes to show that you can absolutely wear tulle and not have it all be see-through. It’s always a good thing to leave things to the imagination.

Angelina Jolie – 2012

Yes, yes, we just said Angie knows how to put her best look forward. Yet, here we are, in 2012, with her actually putting her best LEG forward. Angie, darling, what was going on this night?! Why is your LEG the star of the show?! This Oscar look has been memed into eternity!

Angelina Jolie – 2012

While the dress itself wasn’t terrible, it was the alluring slit and what Angie kept doing with said slit and her leg that made this such a memorably bad outfit. That pose will never be forgotten! We’re sure she’s learned a thing or two about dresses and slits by now.

Charlize Theron – 2004

And here, Charlize makes the nice list! This was her night, as she walked off with the Best Actress Oscar for her role in Monster. It’s amazing to think that here she is in this stunning sparkly Gucci dress, showing off her slim figure, yet for the role, she had to gain 30 lbs!

Charlize Theron – 2004

The dress had embellishments of crystals, and the tan color complimented her skin. Did you know she even had to be sewn into the dress?

Cher – 1988

Designer Bob Mackie certainly created a one-of-a-kind dress this time around. Cher’s designer of choice wanted to make sure she’d win her Oscar in her own special style, and he succeeded. Although Cher won Best Actress for her role in Moonstruck, how many more people remember the dress rather than the award?

Cher – 1988

We gotta hand it to Cher, though; she’s got guts! And with a body like hers, who wouldn’t want to show it off?! We just have to know, was she able to wear any underwear?

Cindy Crawford – 1991

Sometimes, even supermodels get it wrong. The model with the mole sadly chose an ill-fitting dress to attend the Oscars. The color suits her well, as does the bouncy hairdo, but the top half of this red sock (that’s what it looks like) just doesn’t fit right.

Cindy Crawford – 1991

Thankfully, Cindy learned a few things and got it right a few years later with the white bandage dress.

Gwyneth Paltrow – 2002

Uh-oh! It seems our Oscar winner tried the daring route and failed miserably. This Alexander McQueen dress with a mesh top just raised eyebrows at the 74th Academy Awards.

Gwyneth Paltrow – 2002

Gwyneth is a gorgeous woman, and this goth look – whoever’s idea it was – just didn’t do her any favors. It’s since been revealed that she wished she wore a bra. We do too.

Jennifer Lopez – 2015

Everything is golden on Oscar night, right? So why not have a dress to match? JLo wins again with this incredible dress designed by Elie Saab.

Jennifer Lopez – 2015

The plunging neckline and exquisite beadwork are enough to make anyone feel like a princess in this dress. Jennifer’s simple ponytail and nude makeup make sure the dress is the star of the show.

Kate Hudson – 2014

Yes, Kate!! Coming back with a winner this time and a vintage-style Versace number, she glows on the red carpet! The plunging neckline and draped cape complement the whole outfit.

Kate Hudson – 2014

The accessories of a matching purse, some pretty sparkling bits, and the side-swept hair make for a memorable outfit well deserving of a place on the best-dressed list.

Lady Gaga – 2015

We know Stephani Germanotta likes to make a statement. Remember the meat dress? This monstrosity she wore to the 2015 Oscars has us wondering why she wanted to hide her lovely figure. It looks so heavy and must have been exhausting to wear for so long.

Lady Gaga – 2015

And what was she planning with those musketeer-style gloves? Did she sneak in some of her own snacks? Or maybe she tried to sneak some out?

All The Women In Ryan Reynolds’ Life Before Blake Lively

By Thalia Shepherd – 3/23/20

Ryan Reynolds could’ve been a contender for the “Most Eligible Bachelor” award, but he has always been in a relationship. The Deadpool actor is going on his eighth year of perfect marriage with Blake Lively, but before his marriage he had his fair share of relationships and flings. Check out who he’s dated in the past!

Melissa Joan Hart – 1996

The two actors met on set when they were filming the movie Sabrina, the Teenage Witch back in 1996, and they had a super passionate fling that ended up being short-lived. After all, they were only teenagers at the time.

Melissa Joan Hart – 1996

Nonetheless, their short fling did leave a mark on them both. It might be safe to say that this was Ryan Reynolds’s first relationship with a fellow actress?

She Shared More Years Later

It would take a few years before more secrets surfaced surrounding the nature of Melissa Joan Hart’s relationship with Ryan Reynolds. In her 2013 memoir, Melissa Explains It All: Tales from My Abnormally Normal Life, the actress elaborated on her brief romance with Reynolds.

She Shared More Years Later

“Nobody looked as good with wavy blond locks and a thumb ring as Ryan did,” she wrote. “Though I was madly in love with James, my boyfriend of six months by then, Ryan and I spent plenty of time together.”

Melissa Joan Hart – Now

Melissa Joan Hart met her current husband, Mark Wilkerson, at a concert for charity where he performed in a band named Course of Nature in Kentucky back in 2002.

Melissa Joan Hart – Now

The two tied the knot in 2003, and they are still married today. They have three kids together, and the whole family lives in Westport, Connecticut. It seems that her life took a successful turn when she met her husband and started a family.

Traylor Howard – 1998

Ryan Reynolds’ first major gig was a TV show called Two Guys, A Girl, and a Pizza Place back in 2000. It was on that set where he met Traylor Howard. His relationship with Traylor, who was ten years older than him, came to an end after eight months.

Traylor Howard – 1998

Having a relationship with an older woman might be tough, even for an experienced guy like Reynolds. Regardless, the couple lasted for almost a year.

They Kept Things Professional

Despite things not working out between Ryan Reynolds and Traylor Howard, they still managed to keep things relatively professional while working together on Two Guys and a Girl.

They Kept Things Professional

They remained co-stars until 2001. However, many have speculated that the lack of romantic storylines between the two of them might have been influenced by the breakdown of their real-life relationship. Of course, their characters end up with other people by the end of the series. But was that the end of their romance?

Traylor Howard – Now

Traylor Howard is a divorcée, and she might be currently single. She was married to Jarel Portman, whom she married in 2011. Till the present day, she has been married three times and has two children from previous marriages.

Traylor Howard – Now

Traylor gave birth to her daughter in 2006, and her son in 2012. She was also rumored to have dated George Clooney at one point, but we won’t get into that here.

Kristen Johnston – 1999

Ryan Reynolds knew how to attract the TV stars in his life. After the break-up with Traylor Howard, he reportedly started dating Kristen Johnston, the actress from 3rd Rock From the Sun, back in 1999.

Kristen Johnston – 1999

The couple went to the premiere of the Green Mile together. The duo was a surprise couple in Hollywood back in the day.

She Only Has Good Things to Say

While the details surrounding their brief relationship have been cloudy for years, Kristen Johnston recently revealed some more about her time with Ryan Reynolds.

She Only Has Good Things to Say

She started to open up a little about it during an episode of Watch What Happens Live. In short, she only had good things to say to Andy Cohen about what it was like to date the Deadpool star. “It was so long ago I forgot, but literally, so nice, great guy, lovely,” she said. “Lovely person.”

Kristen Johnston – Now

In recent interviews, the actress confessed that she had a past addiction to alcohol and painkillers – but now she has been sober for more than a decade. She also encourages people who are suffering from addiction to bravely speak out and seek help.

Kristen Johnston – Now

The actress dated David Newson in 1996 and Ryan Reynolds in 1999. She has never been married. We wish her all the best and hope she will keep up the good work in supporting people who suffer from addiction.

Rachael Leigh Cook – 2001

Rachael Leigh Cook was the nerdy girl in She’s All That until Freddie Prinze Jr. took off her glasses. Apparently, after Ryan Reynolds broke up with Kristen Johnston, he had a brief fling with Rachael Leigh Cook in 2001.

Rachael Leigh Cook – 2001

Ryan Reynolds is the man when it comes to snagging film and television stars; he never rests. Sadly, his relationship with Rachael didn’t last as long as everyone hoped it would.

Two Big Stars at the Time

Truth be told, both Rachael Leigh Cook and Ryan Reynolds have been coy about the details surrounding their short-lived relationship back in the early 2000s.

Two Big Stars at the Time

What we do know is that the two hit it off just before Reynolds had his breakout role in 2002’s Van Wilder. Cook was also hot property in Hollywood at the time, not only for her role in She’s All That. She also starred in the movie Josie and the Pussycats.

Rachael Leigh Cook – Now

Rachael Leigh Cook married actor David Gillies back in 2004. They started dating right after she broke up with Ryan Reynolds back in 2001. They have two children together, a daughter who was born in September 2013, and a son who was born in April 2015.

Rachael Leigh Cook – Now

Sadly, the couple announced the end of their marriage in June 2019. The couple respectfully decided to go their separate ways. Currently, the actress is single, and there is no sign of a man in her life.

Tara Reid – 2002

In 2002, Ryan played the lead role in the movie National Lampoon’s Van Wilder. Opposite him was Tara Reid, who played his love interest – and their chemistry was excellent.

Tara Reid – 2002

We were all quite surprised that these two never officially became a couple, even though they were both single at the time. Rumor has it that they had a short affair behind the scenes. We find this quite easy to believe, especially when we consider how Ryan seems to have a thing for blonde co-stars.

Rumors Spread Like Wildfire

While the rumors of their off-screen relationship were unconfirmed, the chemistry between Tara Reid and Ryan Reynolds on the set of Van Wilder was unquestionable.

Rumors Spread Like Wildfire

The fact that their characters hit it off in the movie definitely fueled those rumors at the time. Their shared appearance on TRL also made many curious about the nature of their relationship. Of course, Tara Reid was a sought-after comedy star around the same time as Reynolds due to her role in the American Pie film series.

Tara Reid – Now

Since then, Tara has had quite an active love life. In 2010, Tara got engaged to Michael Axtmann, but the two called it off just 3 months later. She then started dating Michael Lillelund late in 2010, and claimed that she married him in August 2011. Strangely, he has denied this.

Tara Reid – Now

Later in August 2011, Tara said she married Zachary Kehayov, but later said it was not a legal marriage. In 2013, she began dating musician Erez Eisen. They stayed together for around a year. We are not aware of any relationships she’s had since then, as Tara seems to have kept her romantic life off the public radar.

Alyssa Milano – 2002

The early 2000’s saw Ryan acting in plenty of rom-coms. One of these was Buying the Cow in 2002. He was cast as a stereotypical womanizer opposite Alyssa Milano, of Charmed fame.

Alyssa Milano – 2002

In the film, the two connect – and the fireworks were easy to see. This set the gossiping tongues wagging. While they made a cute couple in the movie, they claimed that nothing ever went further than the movie set. We guess we will never know – but it would have been interesting to see what would have happened if they had started officially dating.

The Unlikely Couple

There are a couple of reasons why any relationship between Alyssa Milano and Ryan Reynolds around 2002 would have been unlikely. Just a couple of years prior to starring in Buying the Cow, Milano had separated from Cinjun Tate.

The Unlikely Couple

However, it seemed unlikely that she would have started anything with Reynolds seeing that she was dating Charmed co-star Brian Krause at the time. Moreover, Reynolds was in the early stages of his highest-profile relationship yet. But more on that later…

Alyssa Milano – Now

After starring in Charmed, Alyssa became very popular both on screen and off. She dated her Charmed co-star Brian Krause for two years until 2003.

Alyssa Milano – Now

In 2007, she started dating David Bugliari, who proposed a year later. The pair tied the knot in August 2009. The couple have two children and are still happily married as of April 2020.

Alanis Morissette – 2002-2007

There was one woman in the wedding game with Ryan Reynolds even before Blake Lively and Scarlett Johansson. That’s right, Alanis Morissette was engaged to Ryan Reynolds from 2004 until 2007. Their relationship lasted for five years total, but they never went down the aisle. However, Reynolds has declared that he feels like they “were married too.”

Alanis Morissette 2002-2007

The couple announced their separation in February 2007. That must’ve been a really tough punch for Alanis. After the breakup, she wrote a song about Reynolds in which she grieved over their former relationship and how much he meant to her. The song “Torch” appeared in her album Flavors of Entanglement, and she admits that she wrote the song for him.

So Close, Yet So Far

Many have wondered why things ended so abruptly between Alanis Morissette and Ryan Reynolds after being engaged for a handful of years. Since then, the Canadian singer has admitted that she blames herself for things going south.

So Close, Yet So Far

“I get angry at myself for staying in relationships way too long,” she told Women’s Health. However, Morisette also suggested that maybe the two didn’t have enough in common, as well as a potential power struggle between the two towards the end of their engagement.

Alanis Morissette – Now

Alanis Morissette married Mario Treadway, aka Souleye, who is an American hip-hop artist and rapper. They wed in a small, private ceremony at their home in Los Angeles in 2010. They have three children together – the oldest was born in December 2010, then another in 2016, and their most recent baby was born in August 2019.

Alanis Morissette – Now

It’s safe to say that her life took a positive turn after the sad break-up with Ryan Reynolds. She deserves nothing but happiness with her husband and her kids.

Kristin Booth – 2003

We all know Ryan loves acting in rom-coms and comedic action movies. So when he starred in Foolproof in 2003, we can hardly say we were surprised. What did surprise us was his on-screen chemistry with Kristin Booth.

Kristin Booth – 2005

In the film, the two carry out grand heists together – and we couldn’t help noticing what amazing partners they were. Many fans hoped their chemistry would move off screen. Although some sources stated that their friendship was developing into something “more,” nothing was confirmed. This may have been due to his long relationship with Alanis hanging in the balance.

Fans Shipped Them

While many fans of Foolproof shipped a relationship between Kristin Booth and Ryan Reynolds, they would be setting themselves up for failure. This was because Reynolds was in the middle of his engagement to Alanis Morissette.

Fans Shipped Them

While that didn’t exactly end well, there was no chance that Reynolds was going to jump ship that easily with Booth. Of course, Reynolds’s career has gone in a very different direction compared to Booth’s, but this still begs the question: what is she doing now?

Kristin Booth – Now

After filming Foolproof, Kristin went on to act in a few more films, including At Home By Myself… with You and The Calling, which was her last big-screen film.

Kristin Booth – Now

When it comes to her love life, Kristin has mostly kept mum. But we do know that she married musician and composer Tim Ware in 2006. They reportedly don’t have any children as of April 2020.

Amy Smart – 2005

While filming Just Friends in 2005, Ryan worked closely with actress Amy Smart. They had great on-screen chemistry, causing viewers to laugh so hard they cried.

Amy Smart – 2005

The film was a huge commercial and critical success and saw Reynolds play the hopeless romantic Chris Brander who, after being apart from his childhood friend for many years, is determined to make her fall for him. Truth be told, Smart was another female co-star that many speculated was having an off-screen romance with Reynolds. But was it true?

Just Friends?

Rumors circulated that the two were more than just friends. Both denied the allegations, of course, and we will have to be satisfied with never actually knowing.

Just Friends?

Once again though, this seemed unlikely seeing that the actor was in the middle of his engagement to Alanis Morissette. It made sense for Smart to star in Just Friends alongside Reynolds, seeing that she had starred in another successful comedy just a few years prior in Road Trip. But what has Amy Smart been doing since then and where is she now in life?

Amy Smart – Now

Since then, Amy has gone on to act in many popular movies including The Single Moms Club and Avengers of Justice: Farce Wars. She has also been seen in episodes of Shameless and Justified.

Amy Smart – Now

Unlike most people with an active career in Hollywood, she has kept her love life a secret – so we are unsure of her current relationship status.

Scarlett Johansson – 2007-2010

Ryan Reynolds jumped from one serious relationship to another, with Scarlett Johansson this time. The couple did tie the knot, but they’ve kept the marriage very secretive, away from the red carpet and the paparazzi. They were married for two years.

Scarlett Johansson – 2007-2010

Apparently, the main reason for their divorce was the fact that they had to maintain their relationship over a long distance for much of the time – and Scarlett didn’t love this arrangement. After his marriage ended with Scarlett Johansson, Ryan said that he would never marry again.

Why Did They Split?

One of the other factors that led to Scarlett Johansson’s separation from Ryan Reynolds was their rumored competitive streak. Moreover, it is believed that they fought a lot.

Why Did They Split?

Since then, Johansson has admitted that her young age during her marriage to Reynolds had a part to play in it not working out. “I mean, the first time I got married I was 23 years old,” she told Elle magazine. “I didn’t really have an understanding of marriage. Maybe I kind of romanticized it, I think, in a way.”

Scarlett Johansson – Now

After the marriage ended with Reynolds, the actress started dating French businessman Romain Duriac, from 2014 to 2017. The two had a baby together before they split up – a daughter named Rose Dorothy Dauriac, who was born in 2014 in New York City.

Scarlett Johansson – Now

Scarlett Johansson started dating Colin Jost in 2017, and they are currently engaged. Looks like Scarlett will be tying the knot again, and hopefully this one will be a keeper.

Isla Fisher – 2008

Back in the day, Reynolds starred in the popular movie Definitely, Maybe alongside Isla Fisher. The romantic comedy had us all laughing and cooing as the two went through their journey of falling in love.

Isla Fisher – 2008

Of course, it wasn’t that hard to see the amazing chemistry these two shared on screen. While nothing has ever been confirmed about the two, we can’t help but think they would have made a cute real-life couple.

Isla Fisher – Now

Isla met Sacha Baron Cohen in 2002 in Australia. They dated for two years before getting engaged in 2004. The two tied the knot in a Jewish ceremony in 2010, and they now have three children.

Isla Fisher – Now

Isla still acts on screen, and has recently been in the series Arrested Development and a few movies including Keeping Up with the Joneses and The Beach Bum.

Sandra Bullock – 2011

2011 was the year of love and romance for our guy, Ryan Reynolds. After dealing with the divorce from Scarlett Johansson, he had a few flings before he got together with Blake Lively. One of these was a short fling with the famous actress Sandra Bullock.

Sandra Bullock – 2011

Sources said that they were acting flirty when they met in Texas in 2011. However, their relationship was presumed to be just a fling, because shortly after Ryan Reynolds connected with Blake Lively.

Sandra Bullock – Now

Sandra Bullock was married to Jesse James from 2005 until 2010. The couple have two kids together. Jesse James was accused of having multiple affairs with different women and checked in into a rehabilitation clinic to deal with “personal issues.”

Sandra Bullock – Now

Bullock filed for divorce in 2010, citing a “conflict of personalities.” Friends of the actress say that she may marry photographer Bryan Randall, while other rumors say that they were already married in a private ceremony.

Agnes Fischer – 2011

According to People Magazine, Reynolds was seen with the German model Agnes Fischer after his divorce in 2011. Rumors started flying as the two of them were seen together, and many people speculated that they were dating.

Agnes Fischer – 2011

Some rumors say that they dated for only a month. Agnes Fischer is a 34-year old German model who was not on our radar until she started being seen around town with Ryan Reynolds.

Agnes Fischer – Now

Besides Ryan Reynolds, we know that Agnes also had a relationship with Shannon Leto back in 2010. Shannon Leto is an American songwriter who’s part of the band Thirty Seconds to Mars.

Agnes Fischer – Now

According to various sources on the internet as well as her own Instagram page, Agnes Fischer is not currently involved with any men.

Charlize Theron – 2011

It’s no secret that Ryan Reynolds likes to be surrounded by gorgeous actresses and models. In 2011, he had a fling with actress Charlize Theron – and she was the last woman in Reynolds’ life before he married Blake Lively.

Charlize Theron – 2011

According to US Weekly, Ryan and Charlize had different priorities and decided to go their separate ways after dating during the summer months of 2011.

Charlize Theron – Now

After her brief relationship with Ryan ended, Charlize adopted two children in 2012 and 2015. She has been romantically linked to famous actor Sean Penn, who she became engaged to in 2014. However, they called off their engagement in 2015, just six months later.

Charlize Theron – Now

Since then, Charlize has not been seen with any new love interests, choosing instead to focus on her children and her career. She has been in some big movies recently, including Murder Mystery and The Addams Family.

Blake Lively – 2011-Present

Blake Lively is an American actress known for her role in the drama Gossip Girl, in which she played the role of Serena van der Woodsen. She met Ryan Reynolds while they were filming Green Lantern, as they were co-stars. At first, they put each other in the friend zone – but pretty soon, their romance started to warm up.

Blake Lively – 2011-Present

Blake is now the lucky wife of Ryan Reynolds, whom she married in 2012. They already have three kids together. They are one of the most endearing couples in Hollywood, and everyone adores them. The family resides in Los Angeles, California.

Marriage On A Former Plantation

Ryan Reynolds married Blake Lively on a former slave plantation in South Carolina. Some fans were not too happy after they heard this, but it’s their wedding and they should get to do it however they want, right?

Marriage On A Former Plantation

This particular plantation also served as the set for the beloved film The Notebook. That might seem romantic, but not so much when you think about the fact that Blake Lively used to date the star of the film, Ryan Gosling. Ironic choice of location, right?

Morena Baccarin – 2016

You thought the story ended here, but there’s more. At some point, rumors circulated that Reynolds hooked up with his co-star from Deadpool, Morena Baccarin. Of course, Ryan Reynolds denied the rumors on Twitter, and he and Blake continue to be a happy couple.

Morena Baccarin

Unfortunately, being famous and having dated lots of beautiful women in the past tends to attract unwanted attention from the media, as well as unfounded rumors.

Morena Baccarin – Now

After her divorce in September 2015, Morena stated that she was going to marry Ben McKenzie, her Gotham co-star. She was pregnant with their child, a daughter who was born six months later in March 2016.

Morena Baccarin – Now

The couple announced that they were engaged late in 2016 and were married on June 2, 2017 – which is also Morena’s birthday. They were wed in New York and are still happily married today.

Monica Ruiz – 2019

Monica acted in a Peloton ad called “The Gift That Gives Back” in 2019. It created a lot of controversy after its release on television. In the ad, Monica Ruiz is playing a spouse who gets a stationary bike from her husband as a Christmas gift. After the uproar calmed down, Reynolds hired Monica Ruiz for his Gin aviation commercial.

Peloton Controversy?

Of course this sparked rumors that perhaps there was more between the two. Both of them denied it. Ryan stated he was just helping a fellow actor in need. His kindness helped her to relaunch her career.

Monica Ruiz – Now

Monica has been married to Christopher O’Malley since 2013. They have two children together – a daughter and a son.

Monica Ruiz – Now

While she was pregnant, Monica did a lot of maternity modeling. She also starred in a few commercials. She has kept most of her private life out of the limelight, especially since the unfortunate Peloton ad.

The Divorce Rumors

The fans never get tired of inventing rumors about their favorite TV celebrities. The rumors about Reynolds’ impending divorce have been endless, and one of those rumors suggested that Blake got back together with her ex, Leonardo DiCaprio.

The Divorce Rumors

Fortunately, this was not the case – as they are still happily married. In fact, Ryan always makes fun of such rumors and speculations. Maybe the fans should just relax and be content with the fact that Ryan and Blake live a wonderful, happy life together with their children.