Oscar Nominees’ Most Embarrassing Roles: Jennifer Lawrence, Leonardo DiCaprio, and More

Before they were vying for little golden statuettes, this year’s Academy Award nominees appeared in some decidedly worse fare.

02.17.16 12:52 PM ET

On the evening of Feb. 28, Hollywood’s brightest and whitest will don their designer duds and best “surprised” faces and congregate at the Dolby Theatre for the 88th annual Academy Awards. There will be fist-pumping upsets. There will be insane gift bags. And there will, hopefully, be host Chris Rock front and center, skewering the Oscars for the whitewashed circle jerk it’s long been. 

But there will also be nice moments. Stars will be made, tears will be shed, and the world will finally learn how to correctly pronounce the name “Saoirse.” Before Leonardo DiCaprio grew a gross beard and ate raw animal liver or Rachel McAdams gave the best concerned nods you’ve ever seen, these celebrities were once struggling to make a name for themselves, and as such, appeared in pretty ridiculous dreck. So, in honor of the upcoming Academy Awards, The Daily Beast proudly presents its fifth annual edition of Oscar nominees’ most embarrassing roles.

For all the up-and-coming actors out there, don’t worry, it gets better.

Eddie Redmayne, Jupiter Ascending
Oscar Nominee:
The Danish Girl

Rare is the time when an Academy Award nominee also starred in one of the worst movies of the year. Who can forget the inimitable Sandra Bullock appearing at the Razzies to collect her trophy for All About Steve within days of winning the Oscar for The Blind Side, or the Eddie Murphy abomination Norbit, which coincided with his storming out of the ceremony upon losing to Alan Arkin. Well, Eddie Redmayne, who delivered a delicate turn as Lili Elbe, one of the first people to undergo gender reassignment surgery, in The Danish Girl, also made a decidedly less impressive (or more?) bow in the most so-bad-it’s-hilarious movie of the year, Jupiter Ascending. The plot is just too insane to get into here—check out the Honest Trailer, it’s a work of art—but as Balem, an alien heir hellbent on dominating the universe, Redmayne purrs, he hisses, he screams (so, so much), he speaks in a disconcerting whisper, and he treats us to the most over-the-top performance of the year. Ladies and gentlemen, you really need to see this. It’s… something.

Rooney Mara, Law & Order: SVU
Oscar Nominee:

Billed as “Tricia Mara”—a wise choice, in retrospect—one of actress Rooney Mara’s earliest roles was as Jessica Delay, a 17-year-old girl who is found brutally beaten and sodomized by two morbidly obese teens in the 20th episode of Season 7 of Law & Order: Special Victims Unit. Later it’s discovered that the two attackers’ older brother was the victim in a similar attack by Delay and her boyfriend, who despise fat people so much that they post pictures online of themselves giving fat kids beat-downs. “It was so awful,” Mara, who went to on captivate audiences with her brilliant portrayal of icy Goth hacker Lisbeth Salander in David Fincher’s The Girl With the Dragon Tattoo, told Allure. “Me and my boyfriend—although I [didn’t] look old enough to have a boyfriend—went and beat up these fat people, and at the end of the show you find out that I used to be obese and I hate fat people. It’s ridiculous. Who would ever do that? Who would beat someone up because they’re fat?” She’s much, much better in Carol.

Leonardo DiCaprio, Don’s Plum
Oscar Nominee:
The Revenant

This low budget black-and-white film starred real-life pals Leonardo DiCaprio, Tobey Maguire, and Kevin Connolly—aka “The Pussy Posse”—as a group of douchebag Angeleno lotharios who discuss their womanizing ways at an L.A. diner. DiCaprio’s Derek is the worst of the bunch, making a bevy of racist and sexist remarks, and even pushing a girl (played by poor Jenny Lewis) in one upsetting sequence. Don’s Plum was filmed from 1995-1996, when DiCaprio and Maguire weren’t megastars yet, and the actors were only reportedly paid $575 a day for their work. It premiered at the 2001 Berlin Film Festival, but was never released in the U.S. because DiCaprio and Maguire were allegedly so embarrassed by the film—and felt it could harm their burgeoning careers—that they attempted to block its release. Producer David Stutman sued DiCaprio and Maguire, but the group eventually all agreed to release the film outside the U.S. and Canada only.

Jennifer Lawrence, Medium
Oscar Nominee:

Contrary to popular belief, Jennifer Lawrence was not a megastar out of the gate. She appeared in quite a few (little-publicized) things before breaking through with Winter’s Bone, including a fabulous commercial for MTV’s My Super Sweet Sixteen, The Bill Engvall Show, and two episodes of the NBC series Medium. And it was on Medium that she played two outrageous characters—one, a girl who works in a bridal shop who’s gunned down by a crazy person, and the other, an ’80s lovesick teen. In the latter, she performed a rendition of Crowded House’s “Don’t Dream It’s Over” that rivals Katie Holmes’s performance of “On My Own” in pure musical butchery.

Sylvester Stallone, The Party at Kitty and Stud’s
Oscar Nominee:

Sylvester Stallone is a Hollywood legend who probably hasn’t been given enough credit for writing the seminal sports film Rocky, but before that, he was a struggling actor who even found himself homeless, sleeping in New York City’s Port Authority Bus Terminal. Desperate for cash, he starred as the titular Stud in the softcore porn The Party at Kitty and Stud’s, a 1970 movie made for $5,000. “It was either do that movie or rob someone because I was at the end—at the very end—of my rope,” said Stallone. “Instead of doing something desperate, I worked two days for $200 and got myself out of the bus station.” The movie is pretty damn tame, but does culminate in a group sex sequence with Stallone giving his best O-face(s).

Matt Damon, Stuck on You
Oscar Nominee:
The Martian

Matt Damon is one of the most consistent actors in Hollywood today, and probably should’ve won an Oscar for his committed turn in The Talented Mr. Ripley, which has aged gloriously. And he’s been good at comedy in the past, including the Ocean’s films and The Informant, but as one-half of a pair of conjoined twins, probably regrets appearing in this Farrelly brothers’ catastrophe. These days, it’s most notable for a cameo turn by GOP presidential nominee Ben Carson (!) as the surgeon who separates the two idiots.

Brie Larson, 13 Going on 30
Oscar Nominee:

The 26-year-old actress Brie Larson is one of the finest young talents around, and was robbed of an Oscar nod for her riveting portrait of a teen crisis counselor in Short Term 12. Now, she’s the front-runner for the Best Actress Academy Award for her turn as a tortured mom in Room. But before the gal formerly known as Brianne Sidonie Desaulniers was big, and after she released a regrettable bubble gum pop album, Larson starred as an outrageous ’80s mean girl in the underrated romcom 13 Going on 30. This is the opposite of #SquadGoals.

Bryan Cranston, Baywatch
Oscar Nominee:

These days, there’s precious little Bryan Cranston can’t do. He’s had a memorable arc on the greatest comedy series of all-time, gave his all on the coming-of-age show Malcolm in the Middle, and turned in one of the best acting performances in TV history on Breaking Bad. Oh, and he’s won a Tony and is up for his first Academy Award. Geez Louise. But before he hit the big time, Cranston popped up as an Angeleno D-bag who loves fast boats and aviator shades on the hit television show Baywatch. It’s a far cry from Walter White, of course. 

Saoirse Ronan, I Could Never Be Your Woman
Oscar Nominee:

It’s pronounced “SER-SHA,” people. Now that we’ve gotten that out of the way, the Irish actress has risen to become one of the most gifted thesps of her generation, with turns in Atonement, Hanna, and The Grand Budapest Hotel. And she absolutely dazzles in Brooklyn, a film that belongs in the same conversation as Love Story as one of the all-time best onscreen romance stories. But before she was “Oscar Nominee Saoirse Ronan,” she made her big-screen debut in this truly dreadful dramedy from the great Amy Heckerling, who wrote and directed one of the greatest movies of the ’90s, Clueless. In addition to its terrible title, I Could Never Be Your Woman stars Ronan as Izzie, the 13-year-old daughter of Michelle Pfeiffer’s character, who struggles to negotiate puberty and a boy crush. Her bizarre bedroom mirror rendition of Britney Spears is worth a gander.

Rachel McAdams, Shotgun Love Dolls
Oscar Nominee:

Look, no disrespect to Rachel McAdams, who is clearly one of the better actresses around, but before she played the iconic Regina George, romanced RyGos in The Notebook, or starred in the excellent Canadian drama Slings and Arrows, she appeared as the lead in the MTV pilot Shotgun Love Dolls—that thankfully wasn’t picked up. In it, she stars as Beth, a teen who one day learns that she’s living in an alternate universe where she’s the newest member of an all-girls crime fighting squad. Remember that aborted TV show Fox Force Five that Uma Thurman joked about in Pulp Fiction? It’s basically that, only far less cool.