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Bob Dylan in Masked and Anonymous

The easy part was picking Bob Dylan for this list. The difficult part was picking his worst acting job; though the performance the stumbling and fumbling, Empire Burlesque-unleashing Dylan offers in 1987’s Hearts of Fire is beyond unwatchable, what he does in Masked and Anonymous is actually much worse. In the role of Jack Fate – an oh-so-clever name that likely still makes college lit majors swoon – Dylan comes across as the film’s resident street corner weirdo, delivering various aphorisms and other pseudo-philosophical dollops of bullshit in an odd, near-hipster cadence. The polite reviewers called this “enigmatic,” but those not in thrall with All Things Dylan still know better. That deathbed scene where Dylan has to work up some tears? They got chemicals that help the eyes with doing that, you know. Just thank Christ the live songs Dylan and the band perform are good. – Eric Dennis

George Strait in Pure Country

I was raised on country music. In retrospect, it seems obvious that my love for this genre as a child was based largely on the star power of its key performers. Very few country stars throughout the ’80s and ’90s had as much charisma as George Strait, one of country music’s biggest hit makers during that era. Alas, very little of that magnetism came through in Pure Country, the 1992 film about Dusty, a country star tired of bright lights and fame ‘n’ fortune, who sets out on the road to play small honkytonks and rediscover why he loved country music in the first place. I recall even as an eight-year-old thinking that Strait’s performance in this earnest, yet wildly uninventive movie, was, to quote far superior musical artists Wilco, “as cold as kerosene.” The script required that Strait basically play a version of himself, yet he manages to fail even this most fundamental acting test. He relates to his grandmother, his road manager, and his love interest without the slightest hint of pathos. Strait’s performance was too pure, even for country. – Jake Adams

David Bowie in Labyrinth

After 25 years, Labyrinth has left two lasting legacies: Jim Henson’s surrealist muppetry and David Bowie’s man-bulge. As Jareth (which sounds much more like the name of an insurance salesman than a cradle-robbing goblin king), Bowie sings, diddles crystal balls and flashes enough well-defined package that there isn’t much room for acting. Adorned in clingy tights, caked eyeliner and a Tina Turner fright wig, Bowie turns in a cornball performance as one of the least menacing villains of all time. He’s too busy posing and busting out jazz hands during the notoriously goofy “Magic Dance,” to exhibit any semblance of antagonism. His confrontation with an equally dreadful teenage Jennifer Connelly culminates in a whiney stab at nagging her into submission, one that caps a performance worthy of a spot in the Bog of Eternal Stench. – Josh Goller

Jennifer Lopez in Gigli

I never know what surprises me more with Gigli: how awful Jennifer Lopez is in it or how she might be the best thing in the movie. Nevertheless, what makes me hate this performance so much is how much it nakedly displays the narcissism of pop stars infiltrating film. Playing the world’s least convincing assassin and the second lesbian Ben Affleck turned straight with his magic cock, Lopez is too busy adoring herself to bother with anything like believability or chemistry, even with her then-fiancé. Lopez’s self-love is so limitless that she takes on the role of Woman herself, throwing in some pussy power harangues that may well have set women in film back a generation. Masturbatory performances can be fun in their own way, but you’ve gotta give us some foreplay, J-Lo. And no, offering oral sex by way of the phrase, “It’s turkey time – gobble gobble,” doesn’t even remotely count. – Jake Cole

T.I. in Takers

More than other musicians, rappers embody charisma, an intangible quality capable of convincing listeners that a man rhythmically speaking in rhymed patterns is communicating a reality that transcends apparent artifice. Thus, hip-hop superstar T.I. tells us, “This ain’t no album, this ain’t no game, this a trap,” as if the meticulously crafted music was just a front for dealing drugs. T.I.’s immense talent and oversized charisma are precisely what make his turn as a double-crossing member of a bank robbing crew in John Luessenhop’s Takers so disappointing. Already short in stature, T.I. appears positively diminutive, a scrawny nuisance that never threatens the relaxed, urban cool of his co-stars. He gives an annoyingly cocksure performance that, lacking intimidation, suggests the worst, least creative aspects of hip-hop, the ones that inspired early commentators to misguidedly call the art form “faddish.” Despite recording a song as a dialogue between himself and an alter ego (“T.I. vs. T.I.P.”), neither of his personas (much less the creativity behind them) appears here, unforgivable in a film that makes the detestable Chris Brown seem a viable action co-star. Most fittingly: the character T.I. plays is named, of all things, Ghost. – Trevor Link

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Tom Petty in The Postman

There are so, so many good reasons to mock Kevin Costner’s second directorial effort, The Postman. Released in 1997, seven years after he officially became an Academy Award winning director with Dances With Wolves, the movie posits that the clearest route free of post-apocalyptic tribalism is through the inspirational efforts of a stalwart letter carrier reviving the grand, selfless work of the U.S. Postal Service. Whenever I treat myself to the blissful masochism of watching the nearly three-hour film, no single element tickles me more than the “performance” of classic rock icon Tom Petty as the mayor of Bridge City, one of the makeshift communities that sprung up in the wounded world. I put the word above in quotes not just as a slap at the Petty’s acumen, but also as acknowledgement that Petty actually seems to be playing himself. When Costner’s heroic postman first meets Petty’s mayor, he looks him up and down and says, “I know you. You’re famous.” Petty affects the sort of cockeyed grin he usually reserved for his turns as a loopy mad hatter in old music videos and replies, “I was once… sorta.” It’s a brief role and it’s perhaps too much to ask Petty to demonstrate depth of feeling that extends beyond the goof of a cameo the role deserves, but he still ambles through it with a detachment that makes it seem like he wandered onto the set because he spied a craft services truck and Costner put him to work for the hell of it. Still, he’s better than professional actor Will Patton, who plays the villain in the same film with the booming mindlessness of someone trying to intimidate a small child. – Dan Seeger

The Monkees in The Monkees

When the Monkees TV show debuted, Micky Dolenz could barely play the drums, and I’m sure there’s some parallel to be drawn to their acting, but I grew up listening to my mom’s Monkees records and I can’t be mean to the guys that sang such charmingly nonsensical lyrics as, “Cheer up sleepy Jean/ Oh, what can it mean/ To a daydream believer and a/ Homecoming queen?” Nonetheless, in a post-Hard Day’s Night frenzy, some film producers and record executives recruited a cast for a TV show about a band that has wacky adventures. (Think “Flight of the Conchords” but sincere.) Unfortunately, the characters, essentially the actors playing themselves, had the depth of loose leaf, and their timing was so bad that the camera nearly always cuts awkwardly before someone delivers a punchline. The show is hopelessly cheesy. It is only redeemed by some enjoyable bubbegum pop songs and for not being “The Partridge Family.” – Katie Bolton

Mos Def in Be Kind Rewind

Mos Def (soon to be known as Yasiin, apparently) is a talented guy, there’s no disputing that. As a solo performer and half of the legendary hip-hop duo Black Star, he’s built a lasting reputation as a brilliant and socially-conscious rapper. As an actor… not so much. In Michel Gondry’s lukewarm, VHS-nostalgia comedy Be Kind Rewind, Mos Def is flat when he should be active, passive even in the face of Jack Black at his most abrasive and hyper (which is saying something). His motivations are baldly stated, but rarely seem authentic. In fact, it’s the definition of a phoned-in role; rumor has it that his part was originally intended for his buddy Dave Chappelle, which possibly makes his lack of commitment to the role understandable. But until Chappelle makes his own Sweded version of Be Kind Rewind, the movie and Mos Def will remain a disappointment. – Nathan Kamal

DMX in Cradle 2 the Grave

DMX has got to be one of the most unintentionally entertaining rappers, from his frequent run-ins with the law (to put it lightly) to his ignorance (and subsequent incredulity) that there was a man running for President named Barack Obama. Also, he barks a lot. Conversely (and ironically) his acting roles – where he paired up with director Andrzej Bartkowiak for a total of three (!) films – are barely entertaining. The third film in this fruitful collaboration was Cradle 2 the Grave, a film where DMX plays a jewel thief who teams up with an international secret agent (Jet Li) to save the thief’s daughter from an evil Asian man, with multiple sidekicks (Tom Arnold, Anthony Anderson) in tow.

It’s a terrible movie with Jet Li tacked on, but worst of all is the idea that we’re meant to identify with the plight of a man played by DMX. Part of the problem with musicians-turned-actors is that it’s hard to suspend one’s disbelief enough to accept someone like Jon Bon Jovi playing a submarine engineer. Now imagine trying to take DMX seriously – a guy who makes it even harder by being (in real life) an unstable druggie and repeat offender who would go on to attempt to steal a car and pose as a federal agent.That daughter is much safer in the hands of evil Mark Dacascos. – Danny Djeljosevic

Anthony Kiedis in Point Break

In a sense, Anthony Kiedis’ tour de force of overacting in Point Break could be seen as a positive in so much as it only contributes to the campiness factor that makes this early ’90s classic so beloved. That’s really where the positives end for his contribution, as his lack of acting chops stick out like a sore thumb, bitten by a gnarly crab after a long night surfing session. Juxtaposed in all of his scenes by the convincingly scary Warchild (Vincent Klyn,) Kiedis is about as believable as a meth addled surf gangster as Lori Petty is as a leading lady. At least she had the good sense to never dip her toes into the recording studio. – Tom Volk

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Mos Def in The Italian Job

In 2003, it had been four years since Mos Def had released his critically acclaimed record Black on Both Sides. The hip-hop world had waited in anticipation for one of its most prophetic and fiercely political MCs to return to the ring. Instead of making a triumphant follow-up to his breakthrough solo record, Mos Def tried his hand at acting.

Def’s performance in the remake of The Italian Job isn’t bad in the sense that he hams it up; all the ham went to Ed Norton in that one. It’s more that, for an avid political activist, he plays into the Hollywood’s typical black stereotype with ease. Def’s performance plays like a grab-bag of tired racial punch lines. This may not be his worst performance (this list knows there’s plenty to choose from), but it’s one that sinks so far below the ideals of Marcus Garvey that he normally associates himself with, turning in a cheap caricature of “the smooth-talking black guy in a heist movie.” – Kyle Fowle

Keith Richards in Pirates of the Caribbean: On Stranger Tides

Johnny Depp’s portrayal of Jack Sparrow in the Pirates of the Caribbean series was praised by critics for its originality and over-the-top comedic value. The now iconic movie character became similarly beloved by music fans everywhere with the revelation that Depp had based Sparrow’s mannerisms on Keith Richards. A highlight of the series third installment, At World’s End, was a cameo from Richards as Captain Teague, Sparrow’s father. The appearance was short and sweet, not requiring too much from Richards in terms of acting chops.

Despite his total lack of acting experience, the producers pursued Richards for a supporting role in the fourth movie of the franchise. The few additional lines and minutes of screen time Richards was given in On Stranger Tides was enough to ruin the initial fun of seeing him on screen in pirate garb. He isn’t all to blame, as the producers of the Pirates franchise took a non-actor and asked him to walk a fine line between a cameo and legitimate role, a nearly impossible task. Richards’ role in On Stranger Tides is perhaps just a symptom of the attempt to milk every clever joke from the series for all its worth, one of the chief ills of high grossing franchises. – Frank Matt

Britney Spears in How I Met Your Mother

This show isn’t exactly known for its great acting. The main character is the worst actor on the show and at least two of the other four main cast members mail it in every show. So when a guest role sticks out for their bad acting, you know it’s really bad acting. Britney Spears accomplished this in her spot. Her performance was clunky and utterly unconvincing. Her character was awkward and forced. She wasn’t funny and her voice grated the ears. Even the glasses they had her wear just didn’t work, even taking into account that she was supposed to be playing an awkward character. The casting just all together didn’t work and was one of the worst acting jobs by a musician I have ever seen. In an otherwise solid episode, Spears stands out like a turd with diamonds. – Tris Miller

Common in Terminator: Salvation

Terminator: Salvation caught its share of flack for McG’s directing, Christian Bale reading his lines like his script was written in all caps, poor character development and gaping plot holes. Lucky for the film, it was released shortly after the abomination known as X-Men Origins: Wolverine so at the time it didn’t seem half-bad. Still, penetrating the celluloid was the monolith of suck known as rapper Common’s performance. Common’s portrayal of John Connor’s buddy Barnes is the absolute worst performance by a rap artist in a motion picture, and if you’ve ever watched the Starz in Black network, you know that that might be the single meanest thing ever written in the history of this site. Garbled, disinteresting and utterly awful, it made his Gap commercials look like Peter O’Toole. – Chaz Kangas

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Sting in Dune

Poor Gordon Sumner. Who knows how the Brit crooner got wrangled into playing House of Harkonnen heir Feyd-Rautha in David Lynch’s Dune? Although, given writer-director Lynch’s pedigree, it’s not entirely far-fetched to imagine how Sting was lured into playing the antagonist to desert messiah Paul Atreides (Kyle MacLachlan) in the adaptation of the 1965 Frank Herbert sci-fi classic. In fact, the primary surprise is not Sting’s presence in this fundamentally mediocre revision, nor the singer’s fantastic ensemble choices (!), but the short shelf life Lynch allows Feyd-Rautha in the film. Even the essentially poor, campy take Lynch provides ranks a distant second to the radical departures and narrative shortcuts (minimizing faithfulness to the novel) in terms of shock value. Sting is allowed a whole three or four minutes of screen time, room enough to do little more than caper, snarl and pout. And while it’s arguable he should have managed better, Sting’s performance in Dune isn’t the worst among musicians-turned-actors, for at least it leaves Feyd-Rautha’s uncle titillated. But, oh, poor Sting. And, oh, poor David Lynch. – Joe Clinkenbeard

Master P in MP Da Last Don

There are definitely enough examples of musicians making fools of themselves in movies actually released in theaters, but Master P’s turn as Nino Corleone in the No Limit produced MP Da Last Don is such a fiasco that it needs to be mentioned. Written, directed by and starring P himself, this bizarre Godfather remake can barely muster up a 45 minute running time, and the rapper is so lethargic in his role as the Al Pacino-inspired son of an (Italian) mob boss that all questions about the story’s inexplicability are swallowed by the yawning black hole of his performance. – Jesse Cataldo

50 Cent in Streets of Blood

Looks like The Boondocks wasn’t too far off. The biting satire of 50’s distinct mannerisms in the episode “…Or Die Trying,” where he was starring as Air Marshall 50 Cent in Soul Plane 2: The Blackjacking was wonderfully reductive… or so we thought, until we saw him in Streets of Blood. Paired with Val Kilmer, whose sweat and puffiness emote more than him, the two play post-Katrina cops in N’Awlins, solving a murder which they initially thought was random. The movie itself is hilariously bad outright, but 50 himself is impossibly dull. His character barely registers a facial reaction throughout, including when a friend of his is shot by the villain. Throughout the film his character reacts a half-step late, constantly looking befuddled and mumbling his dialogue – presumably the same way he acts in the studio when he’s dropping another thudder. In Streets of Blood he’s textbook amateur, despite having made multiple films before this one. 50 still keeps getting cast, however, so clearly somebody likes his acting chops… I just can’t fathom who that would be. – Rafael Gaitan

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