While not even great actors can hit it out of the park every time, it seems that comedy is especially hard to do well. But when a terrible comedy movie stars an actor who has been honored by the Academy with either a nomination or a win, the contrast between the flop and their previous work can be especially disconcerting.

Here’s a look at 10 terrible comedy movies starring A-list actors. Since we are highlighting comedy movie flops, the films are listed from best to worst, according to critical rankings on Rotten Tomatoes. Films with identical critical rankings are further ordered according to audience approval ratings. Additionally, it should be noted that we are only focusing on films that were made after an actor received critical recognition for their work, since most actors are bound to star in some bombs while they are first starting out in their careers. Unless otherwise indicated, all awards information was obtained from IMDb.

10. The Adventures of Rocky and Bullwinkle (2000)

Robert De Niro had already garnered two Oscar wins and four nominations when he decided to take a role in this forgettable comedy movie based on a long-running cartoon series of the same name. In the film, De Niro plays “Fearless Leader,” the primary antagonist to Rocky and Bullwinkle. While you can hardly fault this accomplished actor from wanting to take a break from his usual dramatic roles, De Niro’s horrible German-accented imitation of his Travis Bickle character from Taxi Driver earned it a spot on this list.

The Adventures of Rocky and Bullwinkle currently has a 43% approval rating from the critics at Rotten Tomatoes who noted that “Though the film stays true to the nature of the original cartoon, the script is disappointing and not funny.” The movie was also a commercial flop that made less than half its production budget, according to Box Office Mojo.

9. The Love Guru (2008)

While Mike Myers plays the starring role in The Love Guru, it was the appearance of Academy Award-winner Ben Kingsley that seemed the most incongruous in this critically panned comedy movie. In the film, Kingsley portrays Guru Tugginmypudha, the teacher of Guru Pitka (Myers). Besides being an overall terrible movie, Kingsley’s role in The Love Guru seems an especially unfortunate career choice for this renowned actor when considering that he won an Oscar for his portrayal of another peace-loving Indian character in 1982’s Gandhi.

While Kingsley wasn’t singled out by the Golden Raspberry Awards – or Razzies – for his role in The Love Guru, the film did earn three awards from the “anti-Oscars” organization in 2008, including Worst Picture. The Love Guru currently has a 14% approval rating from the critics at Rotten Tomatoes.

8. Town and Country (2001)

Multiple Oscar-winning actors and actresses were featured in this critically panned romantic comedy film, including Diane Keaton, Charlton Heston, and Goldie Hawn. However, this flop may have had the biggest impact on Warren Beatty, who hasn’t appeared in a feature film since starring in Town and Country. Although Beatty has never won an Oscar for his acting, he has garnered multiple nominations and won a Best Director Oscar for Reds. He was also given the Irving G. Thalberg Memorial Award in 2000, which is considered an honorary Oscar.

Town and Country was a commercial and critical failure. According to Box Office Mojo, the film cost $90 million to make, but only made $10.4 million in total worldwide gross. The critics at Rotten Tomatoes gave the film a 13% approval rating and noted that “this sex comedy feels confusingly choppy.”

7. Norbit (2007)

Eddie Murphy garnered his first ever Academy Award nomination for his portrayal of soul singer James “Thunder” Early in 2006’s Dreamgirls. In 2007, he earned less desirable accolades from the Razzies, which gave him three awards (Worst Actor, Worst Supporting Actress, and Worst Supporting Actor) for his multiple roles in the atrocious comedy movie Norbit.  Norbit currently has a dismal 9% approval rating from the critics at Rotten Tomatoes, who called it “a cruel, crass, stereotype-filled comedy that’s more depressing than funny.”

6. Man of the House (2005)

Tommy Lee Jones had already earned an Oscar nomination for his role in 1991’s JFK as well as an Oscar win for his performance in 1994’s The Fugitive when he starred in this critically panned comedy movie. In the film, Jones plays a tough-as-nails Texas Ranger who must protect a group of college cheerleaders who are witnesses to a murder. However, unlike his dramatic portrayal of a law enforcement officer in The Fugitive, Jones’s comedic performance as a Texas Ranger in Man of the House failed to impress the critics. Man of the House currently has a 9% approval rating from the critics at Rotten Tomatoes.

5. Crazy on the Outside (2010)

Three-time Academy Award nominee Sigourney Weaver has a major role in this critically panned comedy film that was Tim Allen’s directorial debut. In the film, Thomas Zelda (Tim Allen) tries to straighten out his life after being released from prison, while his sister (Weaver) attempts to cover up his past with elaborate lies. Although Weaver and Allen had previously had success working together in the sci-fi comedy film Galaxy Quest, Crazy on the Outside was poorly received by critics and audiences alike.

Despite featuring a well-known cast that also included Ray Liotta, Kelsey Grammer, and Julie Bowen, Crazy on the Outside only earned a paltry $88,335 in total lifetime gross, according to Box Office Mojo. Crazy on the Outside currently has a low 8% approval rating from the critics at Rotten Tomatoes.

4. Man Trouble (1992)

Jack Nicholson had already won two Oscars and earned seven nominations for his acting when he made this appropriately titled romantic comedy movie flop. In the film, Nicholson plays a roguish dog trainer who falls in love with an opera singer who is receiving death threats. The film was poorly received by the critics and Nicholson’s performance earned him a Worst Actor nomination from the Razzies in 1992.

“Nicholson, as the wise-guy dog trainer, makes a dim attempt to revive his slow-burn sarcasm from the ’70s, but he doesn’t really get any lines; he’s reduced to letting those samurai eyebrows sink wearily into his forehead,” wrote Entertainment Weekly’s Owen Gleiberman in his review of the film. Man Trouble currently has a 7% approval rating from the critics at Rotten Tomatoes.

3. Jack and Jill (2011)

Al Pacino – who is probably most famous for his breakout performance in 1972’s The Godfather – has seven Oscar nominations and one Oscar win. His impressive acting résumé made Pacino’s participation in this famously bad Adam Sandler-directed comedy movie even more perplexing. In the film, Pacino plays a version of himself who is in love with Jill, one of the two title characters played by Sandler. In one depressingly self-referential scene, Jill (Sandler) even destroys Pacino’s Oscar trophy.

Jack and Jill swept the Razzies in 2011 with a record setting ten wins, including a Worst Supporting Actor award for Pacino. Jack and Jill currently has a 3% approval rating from the critics at Rotten Tomatoes who noted that the film “is impossible to recommend on any level whatsoever.”

2. Heart Condition (1990)

Denzel Washington had already earned an Oscar nomination for his performance in 1988’s Cry Freedom and won an Oscar for his performance in 1989’s Glory when he decided to tackle a comedic role in Heart Condition. In the film, Washington plays a dead lawyer who becomes the ghost companion of a racist policeman (Bob Hoskins). This poorly conceived comedy film currently has a bottom-of-the-barrel 0% approval rating from the critics at Rotten Tomatoes.

1. Loose Cannons (1990)

Gene Hackman spent some time slumming in this lowbrow comedy with Dan Akroyd after his first Oscar win. In the film, Hackman plays a tough policeman who comes to realize that his partner suffers from a split personality disorder as they both work to track down a sex video starring Adolf Hitler. Loose Cannons currently has a 0% approval rating from the critics at Rotten Tomatoes.

“For his part, Hackman mostly just stands around watching Aykroyd run through his exertions with the look of a man who has something unspeakable on the sole of his shoe,” wrote The Washington Post’s Hal Hinson in his review of the film. “He shouldn’t even be here and he knows it.”

Follow Nathanael on Twitter @ArnoldEtan_WSCS

Check out Entertainment Cheat Sheet on Facebook!