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VOICE OVER: Kirsten Ria Squibb WRITTEN BY: Taryn Crankshaw
Who says that a rom-com can't be Oscar-worthy? For this list, we'll be looking at romantic comedies that garnered at least one Oscar nomination - and several of which took home the Academy's highest honor. Our countdown includes "Working Girl," "Pretty Woman," "Tootsie," and more!

#10: “Pretty Woman” (1990)

What started as a dark and depressing drama eventually became one of the top-grossing rom-coms of all time. Originally titled “3000,” “Pretty Woman” was the film that launched Julia Roberts as a major box office draw. At only 22 years old when the fiolm was released, she joined Richard Gere to bring the romance between a Hollywood prostitute and businessman to life. With her signature smile, laugh and heart, she made quite an impression on audiences and critics. The trifecta earned her an Oscar nomination for Actress in a Leading Role, which was a big success for Julia and the romantic comedy genre.

#9: “Silver Linings Playbook” (2012)

As one of the most popular rom-coms of the 2010s, "Silver Linings Playbook" dominated the 2013 award show season. The story of a man attempting to reconcile with his ex-wife after completing time in a mental health hospital resonated with audiences. When it came to the Oscars, David O. Russell's picture scored a whopping 8 nominations. The movie's cast, including Bradley Cooper, Robert De Niro, Jennifer Lawrence, and Jacki Weaver, were all in the running for acting prizes, and the film itself was also a candidate for Best Picture. However, "Silver Linings" only took home one award that night, scoring Jennifer Lawrence a Best Actress Academy Award.

#8: “Working Girl” (1988)

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During an era when romantic comedies reigned supreme, “Working Girl” was a standout. The workplace female lead comedy about a corporate secretary assuming the identity of her idea- stealing boss was a big hit in the late 80s. At the 1989 Oscars, the flick’s three female stars, Melanie Griffith, Joan Cusack and Sigourney Weaver, all earned nominations. Director Mike Nichols also swiped himself a credit for Best Director, and the film earned a nod for Best Picture. Keeping with the theme of girl power, the Academy awarded Carly Simon for the film’s theme song “Let the River Run” - the film’s only win, but a memorable one.

#7: “As Good As It Gets” (1997)

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In 1997, "As Good As It Gets" enjoyed major box office success and received considerable attention during the always competitive and whirlwind awards season. The Academy of Motion Pictures Arts and Sciences praised the James L. Brooks directed flick with noms for Best Picture, Writing, and Editing, as well as for the score by musical icon Hans Zimmer. In addition, it also honoured the film's ensemble by nominating its three all-star leads, including Jack Nicholson, Helen Hunt and Greg Kinnear. In the end, Nicholson and Hunt took home gold, proving that two out of three ain't bad.

#6: “Shakespeare in Love” (1998)

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Every year the Oscars are met with their fair share of criticism, and the 1999 ceremony was no exception. When “Shakespeare in Love” won the race for Best Picture, many were left scratching their heads. Industry insiders attributed its win over frontrunner “Saving Private Ryan” to producer Harvey Weinstein’s ruthless campaign. In addition, the film’s star Gwyneth Paltrow won over Cate Blanchett’s highly praised role in “Elizabeth,” and Judi Dench won for only 8 minutes of screentime. Being the first comedy to win Best Picture since 1977’s “Annie Hall,” this should have been a triumph for the genre but instead turned out to be no laughing matter.

#5: “Tootsie” (1982)

Long before it was a Tony Award-winning musical, “Tootsie” was one of the biggest comedies of the 80s. The show biz tale about a down and out actor who disguises himself as a female performer to advance his career starred Dustin Hoffman and Jessica Lange. The acclaimed film racked up a handful of nominations, including Best Picture, Best Director and Best Actor for Hoffman. But out of its 10 nominations, only Lange managed to actually take home the gold. While “Tootsie” still has wonderful moments, it has in more recent years come under fire for its problematic story, demonstrating that comedy doesn’t always age gracefully.

#4: “Moonstruck” (1987)

It was the slap heard around the world, sparking one of the most quoted movie lines ever. 1987’s “Moonstruck” not only struck a chord with audiences but also Academy voters. The rom-com saw Cher as a woman falling in love with her fiance’s brother, played by rising star Nicolas Cage. The film took home 3 out of the 6 Oscars it was nominated for, including Best Supporting Actress for Olympia Dukakis and Best Screenplay for John Patrick Shanley. However, it was Cher’s win for Best Leading Actress that made for one of the most iconic moments in the Academy’s history.

#3: “The Apartment” (1960)

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If there's one thing that is absolutely essential for a romantic comedy to succeed, it's a real chemistry between the leading players. In 1960, cinema legends Shirley MacLaine and Jack Lemmon set screens ablaze with their off the charts dynamic that helped turn "The Apartment" into a classic. Nominated in 10 categories, the film broke even by winning 5, including 3 just for its director/writer Billy Wilder. Although MacLaine and Lemmon did not win their respective categories, they made an impression that still resonates with movie lovers many decades after the film's premiere.

#2: “La La Land” (2016)

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When the musical rom-com “La La Land” strutted onto the silver screen in 2016, industry pundits hit the polls to cast a vote of confidence for the Damien Chazelle flick. With critics and showbiz personnel backing the film, it received an impressive 14 nominations, and it seemed like a Best Picture win was ironclad. During the 89th Academy Awards telecast, the film included wins for Emma Stone, Chazelle and its talented songwriters, among others. When it came time for Best Picture, “La La Land” was declared the winner. However, thanks to a not-so-little slip-up, it was announced live on stage that “Moonlight” was the actual winner. You win some and lose some, but hey, that’s show business. Before we unveil our top pick, here are a few honorable mentions. “When Harry Met Sally…”(1989) Rom-Com Legend Nora Ephron Earned A Screenplay Nomination “Jerry Maguire” (1996) Cuba Gooding Jr. Scored a Memorable Oscar Win “A Touch Of Class” (1973) 70s British Rom-Com Won Glenda Jackson An Oscar “Vicky Cristina Barcelona” (2008) Earned Penelope Cruz A Best Supporting Actress Win “Beginners” (2010) Christopher Plummer Earned His First Oscar Win At 82 Years Old

#1: “It Happened One Night” (1934)

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At the 7th Academy Awards, a romantic comedy called “It Happened One Night” solidified itself as an instant classic. Made only months before the infamously rigid censorship guideline known as the Hays Code came into effect, “Night” was a fun and cheeky romp starring Clark Gable and Claudette Colbert. When it came time for the Oscars, the picture earned nominations for what is known as the Big Five: Best Picture, Best Director, Best Actor, Best Actress and Best Screenplay. The flick broke a record, becoming the first movie to ever win in all of those categories. Since then, there are only two other films in Academy history to have achieved such an honor, with “It Happened One Night” being the only comedy.

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