Movies Like Henry Fool
If you loved Henry Fool's Comedy and Drama storytelling, these films deliver a similar experience — carefully selected for tone, themes, and emotional depth. Each pick includes where to watch it right now.
★ Top Picks

Clean
Tormented by a past life, garbage man Clean attempts a life of quiet redemption. But when his good intentions mark him a target of a local crime boss, Clean is forced to reconcile with the violence of his past.

American Hustle
A conman and his seductive partner are forced to work for a wild FBI agent, who pushes them into a world of Jersey power-brokers and the Mafia.

Sea of Love
Seen-it-all New York detective Frank Keller is unsettled - he has done twenty years on the force and could retire, and he hasn't come to terms with his wife leaving him for a colleague. Joining up with an officer from another part of town to investigate a series of murders linked by the lonely hearts columns he finds he is getting seriously and possibly dangerously involved with Helen, one of the main suspects.

Atlantic City
In a corrupt city, a small-time gangster and the estranged wife of a pot dealer find themselves thrown together in an escapade of love, money, drugs and danger.

Shadow of the Thin Man
High society sleuths Nick and Nora Charles run into a variety of shady characters while investigating a race-track murder.

Cocktail
After being discharged from the Army, Brian Flanagan moves back to Queens and takes a job in a bar run by Doug Coughlin, who teaches Brian the fine art of bar-tending. Brian quickly becomes a patron favorite with his flashy drink-mixing style, and Brian adopts his mentor's cynical philosophy on life and goes for the money.

Tuff Turf
The new guy in a Los Angeles high school, Morgan, does some singing and fights hotshot Nick over disco dancer Frankie.

Young Adult
A divorced writer from the Midwest returns to her hometown to reconnect with an old flame, who's now married with a family.
More Movies Like Henry Fool

Collision
Over the course of one fateful day, a corrupt businessman and his socialite wife race to save their daughter from a notorious crime lord.

You Kill Me
While drying out on the West Coast, an alcoholic hit man befriends a tart-tongued woman who might just come in handy when it's time for him to return to Buffalo and settle some old scores.

Tyler Perry's Madea on the Run - The Play
In trouble with the local authorities, Mabel Simmons, notoriously known as Madea, is on the run from the law. With no place to turn, she moves in with her friend Bam who is recovering from surgery. Unbeknownst to Bam however, Madea is only using the "concerned friend" gag as a way to hide out from the police.

See No Evil, Hear No Evil
A murder takes place in the shop of David Lyons, a deaf man who fails to hear the gunshot being fired. Outside, blind man Wally Karue hears the shot, but cannot see the perpetrator. Both are arrested, but escape to form an unlikely partnership. Being chased by both the law AND the original killers, can the pair work together to outwit them all?

The Machine
Bert Kreischer faces a familial crisis and the arrival of his estranged father when the ghost of his booze-soaked past arrives: a murderous mobster hellbent on kidnapping Bert back to the motherland to atone for his crimes. Together, he and his father must retrace the steps of his younger self in the midst of a war between a sociopathic crime family while they attempt to find common ground.

Diner
Set in 1959, Diner shows how five young men resist their adulthood and seek refuge in their beloved Diner. The mundane, childish, and titillating details of their lives are shared. But the golden moments pass, and the men shoulder their responsibilities, leaving the Diner behind.

The Pink Panther Strikes Again
Charles Dreyfus, who has finally cracked over inspector Clouseau's antics, escapes from a mental institution and launches an elaborate plan to get rid of Clouseau once and for all.

A Walk Among the Tombstones
Private investigator Matthew Scudder is hired by a drug kingpin to find out who kidnapped and murdered his wife.

Criminal
Needing a new partner capable of intricate cons, Richard Gaddis, recruits Rodrigo, a crook with a perfect poker face. The two plan a big-time scam: selling a fake Silver Certificate to currency collector William Hannigan. Rodrigo distrusts his new associate, but needs money to help out his ill father. The situation becomes more complicated when Rodrigo falls for Gaddis' sister, Valerie, drawing another player into the game.

Entourage
Movie star Vincent Chase, together with his boys, Eric, Turtle and Johnny, are back…and back in business with super agent-turned-studio head Ari Gold. Some of their ambitions have changed, but the bond between them remains strong as they navigate the capricious and often cutthroat world of Hollywood.

Easy Money
To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him.

Thunderstruck
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
Why These Movies Are Similar
These recommendations share core qualities with Henry Fool (1998): Comedy and Drama themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of Henry Fool.
See full details for Henry Fool (1998)