Oscar Nominees’ Most Embarrassing Roles, From Benedict Cumberbatch in ‘Zoolander 2’ to Judi Dench’s ‘Cats’

The 94th Academy Awards will be broadcast live from Hollywood on Sunday night, and a dwindling at-home audience will take in the winners, the losers, the tuxes, the gowns, and the hosting trio of Amy Schumer, Wanda Sykes, and Regina Hall . It is still, for all the Sturm und Drang preceding it, the biggest night in Tinseltown. The height of glamour. The pinnacle of the profession.

For over a decade, we have highlighted the most embarrassing roles from the year’s Oscar nominees. It’s not meant to be mean-spirited, but rather a celebration of how far these actors have come from the days when they had to, say, play a pregnant high schooler in a Lifetime movie, or star as a 9/11 truther in an Uwe Boll movie.

And it’s also a good bit of fun.

Plus, now that voting for the Oscars has already passed, it won’t have any sway on their awards prospects. So without further ado, here are the Oscar nominees’ most embarrassing roles.

Benedict Cumberbatch, Zoolander 2

Ben Stiller’s 2001 movie Zoolander was a hilarious, highly quotable send-up of the fashion industry (and featured a dazzling cameo by the late David Bowie). Zoolander 2, released in 2016, was a box-office bomb and one of the worst movie sequels of all time. One of the film’s biggest misses is the character of All, a non-binary model dominating the fashion industry—and played by Benedict Cumberbatch as a creepy alien. When All is introduced, Zoolander and Hansel ask them whether they have “a hot dog or a bun,” among other things. The transgender community and their allies were outraged over the regressive characterization, and Cumberbatch, who’s been nominated for his threatening, closeted cowboy in The Power of the Dog this year, has since acknowledged that it “backfired a little bit.”

Jesse Plemons, VARSITY BLUES

Jesse Plemons first won over audiences as Landry, the bumbling, chivalrous sidekick to QB1 Matt Saracen in Friday Night Lights—or as Ox in LikeMike. He then appeared as a meth dealer in breaking Bad and stole every scene he was in as a creepy cop suffering from board game FOMO in game night. Now, he’s up for his first Oscar as the callow husband who refuses to stand up to his dominating brother in The Power of the Dog. But before FNLhe featured in another football project based in Texas: Varsity Blues. In the 1999 film, a 10-year-old Plemons played Tommy Harbor, the younger brother of Paul Walker’s celebrated QB Lance Harbor, whose only real duty, it seems, is to heckle the second-string QB Jon Moxon (James Van Der Beek ) at a family BBQ.

The 1998 film is so sloppily made that boom mics are visible at several points throughout, and you can even at one point spot a white pillow underneath her shirt.

Kirsten Dunst, FIFTEEN AND PREGNANT

In a storybook twist, both Plemons and his real-life partner, Kirsten Dunst, received their first Oscar nominations portraying a husband-and-wife pair in The Power of the Dog—though let’s be real, she should have been nominated previously for Melancholia. Dunst has been acting since she was very young, making her film debut at age 6 in the Woody Allen-directed segment of New York Stories. During her teen years, however, Hollywood didn’t seem to know what to do with Dunst, resulting in films like The Crow: Salvation and Fifteen and Pregnant, a moralistic Lifetime movie where she played a teen who gets knocked up by her cheating boyfriend. The 1998 film is so sloppily made that boom mics are visible at several points throughout, and you can even at one point spot a white pillow underneath her shirt. Thankfully, one year later she had the much more superior trio of Drop Dead Gorgeous, The Virgin Suicidesand dick. You go, Kiki.

Judi Dench, CATS

One of the silliest things about the ongoing COVID-19 pandemic—a horrible tragedy that’s claimed close to a million American lives—is that the last movie many people saw in theaters before things shut down was Cats, Tom Hooper’s hilariously bad adaptation of the Broadway musical. And look, Dame Judi Dench does her best to make things respectable as the wise cat Old Deuteronomy, but even an actor as great as she could not overcome some of the ghastliest CGI ever committed to film (Hooper infamously made the film’s VFX crew edit out all the cat buttholes in the movie, a very painstaking process). Appearing in Cats is probably the second most embarrassing movie-related thing she’s done, after this.

Will Smith, THE LEGEND OF BAGGER VANCE

If you look up the term “Magical Negro,” you’ll find that it’s a frustrating trope in fiction and cinema where a selfless Black character instilled with mystical powers comes to the aid of the white protagonist, allowing them to realize their greatness. One of the most egregious examples of this trope is Will Smith’s caddie in the period drama The Legend of Bagger Vance, opposite Matt Damon. I’ll leave you with the words of the great filmmaker Spike Lee, who said of the character, “How is it that Black people have these powers but they use them for the benefit of white people?” adding of the film’s Depression-era setting, “Blacks are getting lynched left and right, and [Bagger Vance is] more concerned about improving Matt Damon’s golf swing!” Thankfully, Smith’s had far better luck in sports dramas since, earning an Oscar nod for Ali and another this year for embodying Richard Williams, the father of Venus and Serena, in King Richard.

JK Simmons, POSTAL

German filmmaker Uwe Boll is regarded as one of the worst directors in the history of movies. And Boll was so upset by the way critics gleefully tore apart his tone-deaf films that he challenged several of them to a boxing match (which actually happened). One of Boll’s most notorious entries in the bad-cinema canon is Postal, a 2008 action-comedy adaptation of the video game of the same name. A political satire with little in the way of jokes, the film opens with a rather tasteless dramatization of a hijacked plane going into one of the Twin Towers on 9/11, and manages to get even worse from there. Character actor par excellence JK Simmons pops up as Candidate Eugene Welles, a shameless politician and conspiracy theorist who believes 9/11 was a false flag operation. The movie also features the late Verne Troyer, of Austin Powers fame, being raped by a pack of monkeys. Thankfully, Simmons had Juno come out just prior, so his reputation remained unscathed.

The movie also features the late Verne Troyer, of Austin Powers fame, being raped by a pack of monkeys.

Jessica Chastain, THE HELP

Jessica Chastain exploded onto the scene in 2011 with a trio of films: Jeff Nichols’ apocalyptic drama Take ShelterTerrence Malick’s visually arresting The Tree of Lifeand TheHelp, in which she played Celia Rae Foote, an aspiring socialite in 1963 Mississippi. In true Academy fashion, she received an Oscar nomination for the latter turn, despite showcasing far superior work in the other two. And look, Chastain does the best she can as the comparatively nice Celia, but the film’s overall portrait of Black maids in the civil rights-era American South has aged terribly. As Roxane Gay wrote at the time of its release, “The Help is billed as inspirational, charming and heartwarming. That’s true if your heart is warmed by narrow, condescending, mostly racist depictions of Black people in 1960s Mississippi, overly sympathetic depictions of the white women who employed the helpthe excessive, inaccurate use of dialect, and the glaring omissions with regards to the stirring Civil Rights Movement in which, as Martha Southgate points out, in Entertainment Weekly‘…white people were the help,’ and where ‘the architects, visionaries, prime movers, and most of the on-the-ground laborers of the civil rights movement were African-American.’”

Nicole Kidman, GRACE OF MONACO

With its combo of filmmaker Olivier Dahan (Life in pink), distributor Harvey Weinstein, and the great Nicole Kidman playing the titular Grace Kelly, many felt that Grace of Monaco was poised to be an Oscar hopeful. After its disastrous opening at the Cannes Film Festival, however—owing to cuts demanded by notorious meddler Weinstein—expectations were readjusted. The movie ended up receiving no theatrical release stateside, instead premiering on Lifetime in 2015 and earning a 9% rating on Rotten Tomatoes. Hilariously, the film still garnered an Emmy nod for Outstanding Television Movie, which just goes to show how awards ceremonies will nominate anything to attract A-listers to the telecast. Kidman, of course, quickly rebounded from the catastrophe with a Best Supporting Actress Oscar nod a year later for Lion. Weinstein, on the other hand, is rotting away in prison after being convicted of rape.

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