The Top 15 Hottest Female Oscar Winners

Oscar season is upon us, so that means one thing: obligatory lists about the top Academy Award winners of all time. Here at The Richest, we are no different, but we do have our own twist. While many people would find it tempting to compare Best Picture or Best Director, we, instead, choose to focus on what’s really important: who is the hottest Oscar winner of all time?

While this loaded question may not be possible to answer, since everyone’s tastes are different, we can certainly narrow the field down to the top 15. From Grace Kelly’s classic beauty to Jennifer Lawrence’s girl-next-door quality, we’re going to count down the most beautiful faces to ever grace the silver screen. To keep things relatively fair, we’re going to list these buxom beauties in chronological order. This is to prohibit anyone from disputing who is actually hotter, Catherine Zeta-Jones or Penelope Cruz and instead leave it to your imagination.

15. Penelope Cruz – Vicky Cristina Barcelona (2008)

Earlier, we remarked at how Catherine Zeta-Jones’ accent makes her sexier than she would be without one. In Penelope Cruz’s case, that sentiment is repeated twofold. There’s nothing quite like a beautiful Latin woman with a thick, Spanish accent. Coupled with her exotic good looks, and you have a force to be reckoned with. This Spanish Enchantress made a name for herself in her native Spain for years before becoming noticed in the States. It wasn’t until after working with the legendary Pedro Almodovar that she gained international fame. Since then, films like Vanilla Sky (a remake of a Spanish film also starring Cruz), the latest Pirates of the Caribbean, and now the second Zoolander, means that this Latin beauty is here to stay. She won her Oscar for her performance in the critically acclaimed Vicky Cristina Barcelona.

Fun Fact: Cruz is only the second Spanish actor to be nominated for an Oscar, the first being her husband, Javier Bardem, who also co-starred in Barcelona.

14. Natalie Portman – Black Swan (2010)

Known best for being a key character in the Star Wars prequels, Portman got started in Hollywood at a young age, with her first starring role in Leon: The Professional. From there, she developed into a gorgeous woman, who’s petite physique and infectious smile entrances everyone. Portman has had a fascinating career, mixing artful films like Black Swan and Garden State with much more popcorn fare, like the aforementioned Star Wars and Mars Attacks. It was her performance in Swan, however, that cemented her star status with an Oscar win for Best Actress. Even though the film is mostly memorable for her love scene with Mila Kunis (were we watching it on VHS, it would be completely worn out by now), the Academy felt it necessary to bestow the gold upon her in 2010.

Fun Fact: Prior to being in the prequels, Portman had never seen a Star Wars film, confusing it with Star Trek.

13. Angelina Jolie – Girl, Interrupted (1999)

It’s hard to imagine Angelina Jolie as anything but a mother and philanthropist these days, but there was a time when she was a feisty, incredibly sexy girl who played by her own rules. During her famous marriage to Billy Bob Thornton, she engaged in some questionable activities, making her one of Hollywood’s bad girls. It was fitting, then, that she won an Oscar for playing an unhinged woman in a mental institution in the film Girl, Interrupted. It wasn’t until she visited Cambodia for Tomb Raider that she settled down.

Fun fact: her performance in Girl earned her the coveted “triple crown”, which refers to when an actor/actress wins all three Golden Globe, SAG, and Academy Awards.

12. Halle Berry – Monster’s Ball (2001)

While most people recognize Berry as Storm from the X-Men films, Halle has had a long and moderately successful film career, showcasing her talents in films like Bulworth and Monster’s Ball, and showcasing her sexiness in movies like The Flintstones (seriously) and Catwoman. Able to work both seriously and with tongue firmly in cheek, Berry’s career has certainly had its share of highs and lows. Her career high came when she won the Best Actress Oscar for Monster’s Ball, becoming the first and only black actress to do so.

Fun Fact: Halle was so committed to her first film role as a crack addict in Spike Lee’s Jungle Fever, she refused to bathe for several days.

11. Audrey Hepburn – Roman Holiday (1953)

As the prettier of the two Hepburns (Katherine being the other, although there is no relation), Audrey made her mark in Hollywood as the classy girl, the girl you would want to be seen with at your side. Born into wealth, she always exuded confidence and grace both on the screen and off. While most people remember her for her form-fitting black dress in Breakfast at Tiffany’s, her stardom started eight years prior, with the huge hit Roman Holiday. She won the Oscar for Best Actress for her role as Princess Ann. The win cemented her celebrity status, and she was forever ensconced in the American lexicon.

Fun Fact: Hepburn was her stage name, as she was born Audrey Ruston in Belgium.

10. Grace Kelly – The Country Girl (1954)

Of all of the women on this list, only one can boast the title of princess. Grace Kelly was a prolific film actor in the mid-50s, starring alongside such heavyweights as Clark Gable and Cary Grant. However, her film career was cut short when she met the Prince of Monaco at the Cannes Film Festival in 1955. He was smitten and offered his hand in marriage. Kelly agreed and traded her glamorous life in Hollywood for a glamorous life on the French Riviera. Many would agree that is a step up. Grace had a classic style and beauty all her own, making her short tenure in the limelight that much brighter. She won an Oscar for her role in the film The Country Girl.

Fun Fact: It was this movie shown at Cannes, where she would meet her future husband.

9. Sophia Loren – Two Women (1961)

There are two things that Italy is known for: beautiful cars and beautiful women. One could argue that its food is also noteworthy, but let’s instead focus on one of the prettiest exports of the country, Miss Sophia Loren. Her name is almost as beautiful as her figure, and even today, at 81, she’s still a dynamo. Her exotic good looks captured the eyes of many filmgoers in the 60’s and 70’s, where she was best known for her roles in El Cid and Two Women. It was in the latter that she won the golden trophy in 1961, portraying a war widow named Cesira.

Fun Fact: Loren was discovered in 1948 by the producer Carlo Ponti when she won a local beauty pageant. He helped her break into Hollywood, and in return, she married him. It’s unclear who got the better end of that deal, but we’re leaning towards Ponti.

8. Jane Fonda – Coming Home (1978)

Here we have another oldie but goodie. Daughter of the legendary Henry Fonda, Jane got into acting in her late teens and was most active during the sixties and seventies. While most people would know her from arguably one of her biggest hits, 9 to 5, we instead choose to look at her cheesy, trashy movies like Barbarella (1968). It was in these movies her sex appeal really shined. Afterward, though, seemingly as a way to remove herself from such an image, she started turning in more compelling performances, as well as making headlines with her activism. She won Best Actress for Coming Home in 1978.

Fun Fact: Jane first got into acting in a stage play of The Country Girl, the movie for which Grace Kelly won her Oscar.

7. Kim Basinger – L.A. Confidential (1997)

Skipping right past the soulful Seventies and extreme Eighties, we find ourselves in the late Nineties, drooling over one of the biggest sex symbols of the day, Miss Kim Basinger. She started off her career in modeling, and, suffice to say, she killed it as a model. As for acting, she played around for a while, but it wasn’t until Batman came knocking that she got her big break, as reporter Vicki Vale. Her career high came with L.A. Confidential, playing a hooker with a heart of gold (is there any other kind?). It was enough to win her Oscar gold, as the Academy likes stories of working girls finding happiness (Pretty Woman, anyone?).

Fun Fact: Kim, perhaps having too much money on her hands, bought the town of Braselton, Georgia for $20 million. It’s not exactly clear why, but she wound up having to sell it later on.

6. Jennifer Connelly – A Beautiful Mind (2001)

2001 was a good year, regarding Oscar nominees being easy on the eyes. While Halle was busy winning the Best Actress award, Jennifer Connelly took home the Supporting Actress trophy, for her performance in A Beautiful Mind. If it were up to us, the film would have centered on her and have been called A Beautiful Face, but I guess that’s why we’re not filmmakers. Connelly’s career really started when she was in the successful Labyrinth, and then in The Rocketeer. Her career trajectory has been much more subdued than most on this list, as she chose to pursue smaller, more unique films, rather than blockbuster successes.

Fun Fact: Jennifer attended both Yale and Stanford, studying classical theater.

5. Catherine Zeta-Jones – Chicago (2002)

As far as Oscar-winning actresses go, none is quite as elegant and alluring as Catherine Zeta-Jones. If for no other reason, her soft, silky accent helps her transcend her traditional beauty to become something even better. She broke out in the 1998 film The Mask of Zorro, opposite Antonio Banderas. Since then, she has had a pretty high profile career, starring in the Ocean’s Eleven series as well as Entrapment. Although full disclosure, we only saw the latter because her butt was featured so prominently in the trailer. Jones won her Oscar in 2002 for her villainous role in Chicago (the musical, not the city).

Fun Fact: In 2010, Jones was awarded Commander of the Order of the British Empire for her work in drama. It’s unclear whether the title actually means anything, but it makes one hell of a business card.

4. Charlize Theron – Monster (2003)

While her Oscar performance was not exactly the best example of her beauty, when it comes to actresses in Hollywood whose sexiness transcends language, Charlize is definitely at the top. An impressively tall and captivating person, she has made her mark in the world of film, both showcasing her raw talent and her voracious wit. She feels comfortable in action films, heady dramas, and even farcical comedies, making her one versatile actress. She won the gold in 2003 for her haunting portrayal of a serial killer in the film Monster.

Fun Fact: Charlize was discovered by an agent when she flipped out at an ATM in Hollywood, causing a scene. The agent liked her moxie, so he gave her his card. The rest is history.

3. Rachel Weisz – The Constant Gardener (2005)

Like Angelina Jolie, Rachel Weisz is a “triple crown” winner in Hollywood. For her stellar performance in The Constant Gardener, a film which none of you saw (be honest), she took home a Golden Globe, SAG, and Academy Award. However, what she’s best known for is her adorable, unbelievably cute performance in The Mummy, playing a shy, nerdy girl who winds up saving the world. Since then, she’s proven herself a worthy actress, not to mention a gorgeous one.

Fun Fact: Weisz was almost in The Dark Knight Rises as Catwoman, but had to back out due to scheduling reasons. She is also married to current James Bond, Daniel Craig.

2. Anne Hathaway – Les Miserables (2012)

What makes Anne Hathaway a part of this list is her everyday, girl-next-door good looks. Hathaway has a charm and smile that endears her to her fans and admirers. She has indeed aged well since her major debut in The Princess Diaries. Since then, she seems to feel at home in both comedies like Get Smart, and more arthouse films like Rachel Getting Married. However, it was her acting chops in the over-the-top spectacle of Les Miserables that got her Oscar gold in 2012. Who knew that she could sing so well? Apparently the Academy was impressed, granting her Best Supporting Actress award that year.

Fun Fact: While it’s unknown if this was done on purpose, Anne Hathaway is the same name as William Shakespeare’s wife. So at least she has that going for her.

1. Jennifer Lawrence – Silver Linings Playbook (2012)

Another banner year for hot girls winning coveted awards. While Hathaway was busy winning the gold for Supporting Actress, newcomer Jennifer Lawrence took the big prize for her performance in Silver Linings Playbook. Like Hathaway, Lawrence has a very girl-next-door quality to her beauty, which has served her well thus far. Best known for The Hunger Games, Lawrence has shown not only her beautiful side but her exceptional talent in films like Playbook, as well as Winter’s Bone and American Hustle. She is actually the youngest person to have three Oscar nominations, and she is yet another winner of the “triple crown”, for her role in Playbook.

Fun Fact: On the set of American Hustle, Lawrence stained several dresses due to her insatiable love of Doritos chips.