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

Before achieving Oscar nomination glory, these stars—from Leonardo DiCaprio to Jennifer Lawrence—made some regrettable choices. See the best of the worst.

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Leonardo DiCaprio, Don’s Plum (2001)Oscar Nominee: The Wolf of Wall Street

This low budget black-and-white film starred real-life pals Leonardo DiCaprio, Tobey Maguire, and Kevin Connolly 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 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, Monk (2006)Oscar Nominee: American Hustle

Before she was America’s Sweetheart, winning an Oscar at the young age of 22 for her stunning performance as a Goth-y widow in Silver Linings Playbook, and becoming a global star with The Hunger Games films, Jennifer Lawrence made her TV debut as a rowdy mascot on the USA series Monk. In the episode “Mr. Monk and the Big Game,” Lawrence is seen sporting a cougar costume and jumping on Monk (Tony Shalhoub) as he coaches a high school basketball game. Later, she takes off her mascot head to reveal herself. Coincidentally (or not), one of Shia LaBeouf’s earliest TV roles was also as a high school mascot who gets sidelined with an injury on the cult show Freaks and Geeks.

Jonah Hill, Accepted (2006)Oscar Nominee: The Wolf of Wall Street

Prior to becoming a two-time Oscar nominee for his excellent turns in Moneyball and The Wolf of Wall Street, Jonah Hill was an up-and-coming comedic actor who starred as Sherman Schrader III, an awkward college freshman who tries to blend in at upper-crusty Harmon College by pledging a fraternity. Sherman screams like a girl, and is so desperate to become one of the cool kids on campus (he yells, “Yes! Yes! I want it! I want everything you guys have! I want Lilac shirts! I want visors kinda tilted to the side with hair gel coming out of them!”) that he endures a number of indignities by his fraternity’s douche-y president, Hoyt, including wearing a hot dog suit in the quad and propositioning random classmates to, “Ask me about my wiener!”

Amy Adams, Cruel Intentions 2 (2000)Oscar Nominee: American Hustle

Today, Amy Adams has become one of the finest—and most consistently reliable—actresses in showbiz, racking up an otherworldly five Oscar nominations in just eight years. In her early years as a struggling actress, she was set to star in a TV spin-off of the movie Cruel Intentions called Manchester Prep, which was set to air on Fox. Adams played femme fatale Kathryn Merteuil, a rich-bitch teen who gleefully manipulates her stepbrother, Sebastian Valmont, played by direct-to-video sequel star Robin Dunne (see: The Skulls II, Species III, American Psycho II: All American Girl). Sadly, the series wasn’t picked up by Fox, and was released as a direct-to-video film in 2000. But, with lines like “two’s company, three’s a fuckload of fun,” it’s worth the price of a rental for Adams’s entertainingly over-the-top turn.

Bradley Cooper, Globe Trekker (2000)Oscar Nominee: American Hustle

Prior to becoming a blockbuster star (in The Hangover franchise) and a formidable dramatic actor (in Limitless, Silver Linings Playbook, and American Hustle), Bradley Cooper popped up in a series of odd acting jobs, including the TV film I Want to Marry Ryan Banks, opposite Jason Priestley, and the ill-fated TV series Kitchen Confidential. One of his earliest roles was as a presenter on the British travel-adventure series Globe Trekker. In the Cooper-hosted episode, he visits a (mostly male) nude beach in Veli Losinj, Croatia, and his interactions with the naked townsfolk are priceless. At the end of the episode, Cooper drops trou and dives into the ocean as the sun slowly sets in the background. “You know what? I’m never gonna wear clothes again,” he says in voiceover.

Christian Bale, Shaft (2000)Oscar Nominee: American Hustle

The same year as his star making turn in American Psycho, and before he became a global superstar for the Batman films (and Oscar winner for The Fighter), another less-ballyhooed Bale film was released: Shaft. In the remake, Samuel L. Jackson stars as no-BS detective John Shaft, while Bale is Walter Wade, Jr., a rich racist asshole who beats a black guy named Trey Howard (Mekhi Phifer) to death for calling him out on his racism in front of his white-collar friends. When Howard enters a nice NYC lounge, Wade says to him, “We don’t have any endo here…. Aight?!” Howard replies by poking two holes in a napkin and throwing it over Wade’s head. Later, after he beats Howard to death with a metal pole and the body starts convulsing, Bale’s character remarks, “Homeboy’s got rhythm.” Yikes.

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Matthew McConaughey, Surfer, Dude (2008)Oscar Nominee: Dallas Buyers Club

Matthew McConaughey is currently in the midst of one of the best runs of any actor ever. Last year, he mesmerized audiences in an array of roles including an aging stripper in Magic Mike, a closeted journalist in The Paperboy, a goofy sheriff in Bernie, and a psycho with a fried chicken fetish in Killer Joe. This year, he wowed with roles in Mud, his Oscar nominated turn as AIDS crusader Ron Woodroof in Dallas Buyers Club, and is currently dazzling audiences as an oddball philosophical policeman in HBO’s True Detective. Before his career about-face, he was (unfairly) pigeonholed as an oft-shirtless himbo, and nowhere was this more apt than in the much-maligned Surfer, Dude. In the film, he stars as an airheaded surfer dude suffering an existential crisis, and spends almost the entire film wandering around stoned and shirtless. The movie made just over $50,000 (yes, really) at the box office, and currently holds a 0% rating on Rotten Tomatoes.

Sandra Bullock, All About Steve (2009)Oscar Nominee: Gravity

Sandra Bullock made history when, in 2010, she was the first to receive both the Best Actress Oscar (for The Blind Side) and the Worst Actress Razzie (for All About Steve). In Steve, she plays Mary Magdalene Horowitz, an excitable loser who spends her days confiding in her only friend—a pet hamster. Her parents set her up on a blind date and it turns out to be with Steve (Bradley Cooper), an attractive cameraman for news network CCN. Mary is hooked on Steve from the get-go and, after she tries to jump him in his truck, he makes up a story that he has to go out of town to cover a breaking news story. Mary believes him, and embarks on a wacky, stalker-ish road trip across the country trying to track him down. Mary is unbearably ditzy and painful to watch. But Bullock, ever the sport, accepted the Razzie … in person. She even gave out DVDs of All About Steve to the entire Razzie Awards audience.

Jared Leto, Chapter 27 (2007)Oscar Nominee: Dallas Buyers Club

Jared Leto wows as Rayon, a transsexual diagnosed with AIDS-cum-renegade activist in Dallas Buyers Club—his first film role in six years. The last one, unfortunately, was as John Lennon’s assassin Mark David Chapman in Chapter 27, opposite Lindsay Lohan. Leto gained over 60 pounds for the role, rendering him completely unrecognizable, and turned in a solid performance as the deranged fanboy-killer. Despite Leto’s committed turn, the movie was torn apart by critics, receiving an 18% approval rating on Rotten Tomatoes, and when I interviewed him at TIFF last year, Leto told me his transformation was so convincing that some Hollywood producers actually thought he’d fallen off the deep end and gained a ton of weight, instead of just doing it for the role. Thankfully, he’s back with a vengeance in Dallas Buyers, and hopefully we don’t have to wait another six years for his next onscreen performance.

Julia Roberts, Mary Reilly (1996)Oscar Nominee: August: Osage County

Prior to 1997’s My Best Friend’s Wedding, which ignited a massive series of Roberts hits, including Stepmom, Runaway Bride, Notting Hill, and Erin Brockovich, for which she won an Oscar, Roberts was mired in a bit of a slump. The worst of the bunch was Mary Reilly, a gothic take on Dr. Jekyll and Mr. Hyde. Roberts starred as the titular servant in the dreary drama, with Malkovich as Dr. Henry Jekyll/Mr. Hyde. Roberts and Malkovich reportedly feuded during the making of the film, and have very little chemistry onscreen. Instead, they just engage in a series of boring convos on topics like desire, the soul—you get the picture. Roberts is miscast here, never cracking that blockbuster smile and speaking in a terrible Irish accent. She was nominated for a Worst Actress Razzie for the role.

Meryl Streep, Dark Matter (2008)Oscar Nominee: August: Osage County

The legendary Streep received her record 18th (!) Oscar nomination for her over-the-top turn as an awful Southern matriarch dying of cancer in August: Osage County, and it takes a lot of work to single out even one bad Streep performance (most point to She-Devil, but I thought she was hilarious in it). In the case of Dark Matter, unfortunately, the film remains notorious for reasons entirely beyond her control. Streep plays Joanna Silver, a wealthy university patron who takes Liu Xing (Liu Ye), a Chinese prodigy-college student under her wing. Liu becomes obsessed with the study of “dark matter” and, after being railroaded by his dissertation professor and failing to graduate, shoots up the school. The film premiered at the 2007 Sundance Film Festival and was slated for release that year, but its released date was pushed all the way back to April 2008 because the events too closely resembled the Virginia Tech massacre. When it was finally released, it was panned by critics, receiving a 32% rating on Rotten Tomatoes.