Brooklyn native and former Marine Harvey Keitel made his feature film debut in Martin Scorsese’s first movie, 1967’s Who’s That Knocking At My Door. Since then, Keitel has acted in dozens and dozens of movies, known for his roles in Scorsese’s other films, in Quentin Tarantino’s gangster epics, and in Wes Anderson’s ensemble comedies.

Despite his reputation and notable, expansive filmography, Keitel is one of the few actors of his generation to never win an Oscar, despite receiving a nomination for his role in 1991’s Bugsy. While quite a few of his performances are worthy of the award, he has acted in some real bombs. This list sifts through Keitel’s diverse career, highlighting five of his most laudable roles and five of his most disastrous.

Razzie: Little Nicky (2000)

This devilish Adam Sandler flop features Keitel as the Lord of Darkness himself. Satan is contemplating retirement, and his three sons are competing for the top spot in Hell. While his older sons Adrian and Cassius seem prepared to take on the underworld, his youngest Nicky, played by Sandler, is a total doofus.

Ultimately, Satan decides to wait another 10,000 years before giving up his throne. Adrian and Cassius ascend to New York, where they hope to gather enough souls to take over Hell by force. Satan sends Nicky up to thwart his brothers’ efforts. Needless to say, no one received a standing applause for their contributions to this fiasco.

Oscar: Bad Lieutenant (1992)

Keitel plays the corrupt and vile title character in this Abel Ferrara neo-noir drama. As a police officer who uses his status to exploit vulnerable women and abuse drugs, there is nothing redeemable about the Lieutenant’s choices, and they all come crashing down upon him after he investigates the sexual assault of a nun.

Keitel manages to give depth and dimension to a man whose crimes and indiscretions are unjustifiable, adding nuance to the film’s exploration of good and evil. Keitel’s frequent collaborator Martin Scorsese considers Bad Lieutenant the best film of the 1990s.

Razzie: Crime Spree (2003)

A superficial and derivative crime drama, this film pitches Keitel against a troupe of French criminals played by the likes of Gerard Depardieu and Johnny Hallyday. The Frenchmen cross the Atlantic to complete a heist in Chicago.

However, the heist cuts into funds controlled by Zammeti, Keitel’s character. Zammeti turns out to be the head of a powerful organized crime family, and he puts hits out for the Frenchmen. Soon, the FBI also becomes involved, and the European visitors are caught between a rock and a hard place. You can file this one under “Long-Forgotten Secondhand Heist Films.”

Oscar: Blue Collar (1978)

Paul Schrader, whose screenplays for Taxi Driver and Raging Bull set the tone for Martin Scorsese’s career, made a big impact with his directorial debut about autoworkers in Detroit. Keitel stars alongside Richard Pryor and Yaphet Kotto as Checker Cab assembly linemen. Despite having full-time work and union representation, they all struggle to make ends meet.

The men decide to steal cash from their local union’s safe, and they discover union bureaucrats have been siphoning funds from workers for quite some time. Things come to a head as the men are pitched against each other in the wake of the robbery, and the film gives a searing examination of the ways capitalism incites racial and class-based antagonism. As a descendant of Polish immigrants named Jerry, Keitel gives an impactful, raw performance.

Razzie: Finding Graceland (1999)

In this silly, kitschy road trip movie, Keitel plays a hitchhiker who claims to be Elvis Presley. He’s picked up by Byron, portrayed by Jonathon Schaech, on his way to Memphis, Tennessee. Keitel’s character asks Byron to take him home to Graceland.

Elvis claims to have staged his own death, and the two men hit the road, meeting some other strange characters along the way, including a Marilyn Monroe impersonator. Full of pseudo-rocking scenes and oozing with misguided nostalgia for bygone eras, the film’s pointlessness knows no bounds. Keitel is many things, but this New Yorker is not the King of Rock’N’Roll.

Oscar: The Piano (1993)

A period piece from New Zealand director Jane Campion, The Piano is a sultry, romantic drama that brings two disparate people together through a piano. Holly Hunter plays a psychologically mute woman named Ada who moves to New Zealand with her young daughter and new husband Alisdair Stewart, who arranged the marriage by paying Ada’s father.

The only thing Ada enjoys in life is her piano, which Stewart refuses to let her bring home. Instead, he gives the piano to overseer George Baines, played by Keitel, a retired sailor who has adapted native Maori customs, including tattooing his face. Baines hires Ada to teach him to play the piano, in turn reuniting her with her beloved instrument. As they spend more time together, intense lust grows between them, and both Keitel and Hunter give racy, evocative performances.

Razzie: National Treasure (2004)

The National Treasure Disney franchise brings together revisionist US history, Freemasons, and Nicolas Cage. Cage plays Benjamin Franklin Gates, a cryptozoologist and treasure hunter looking to recover a trove of hidden treasure entombed by Freemasons during the American Revolutionary War.

Whoever can find the Declaration of Independence first and decode the map on the back of it will get the goods, and Gates is thwarted by other treasure hunters and government officials, like Keitel’s FBI Agent Peter Sadusky. Tame and innocuous, this family-friendly film is marked by dull performances.

Oscar: Mean Streets (1973)

Keitel’s portrayal of Italian-American Charlie in this gritty early masterpiece from Martin Scorsese deserves more recognition than it has received. Frenetic and palpable, the tone of Mean Streets matches its title. Scorsese grew up in New York’s Little Italy, where the film occurs, and he pays homage to the neighborhood’s thriving corridors and seedy underbelly.

In the film, Charlie works for his Uncle Giovanni, a mobster, loan shark, and political fixer. His best friend, Johnny Boy, played by Robert De Niro, is becoming more corrupt and unhinged because of the nature of their work. Charlie tries to reconcile devout Catholicism with his morally questionable means of making money.

Razzie: Saturn 3 (1980)

Saturn 3 is a calamitous British science fiction film about scientists on Saturn’s third moon. Kirk Douglas and Farah Fawcett are living outside Saturn, tasked with creating new food sources to return to Earth. Keitel plays a third scientist, Benson, who arrives with a robot that transforms into a nefarious machine after communication with Earth is severed.

Even though the screenplay was written by acclaimed British novelist Martis Amis, it’s still considered a sloppy deep space film. Keitel, who refused to participate in post-production looping, had his voice dubbed by a British actor because the film’s director, Stanley Konen, wasn’t happy with Keitel’s Brooklyn accent.

Oscar: Clockers (1995)

Keitel is phenomenal in this Spike Lee joint that investigates the nature of violence within urban black communities. The film’s action is structured like a police procedural, but it’s really a political and social call-to-arms.

Keitel plays police officer Rocco Klein, who questions a 19-year-old low-level drug dealer named Spike, played by Mekhi Phifer, after a man Spike is associated with ends up dead from a bullet wound. It turns out Spike was coerced into the act by his boss, a drug kingpin named Rodney. Instead of just locking up another young black man, Klein works with Spike to help him find a way out.