Best movies like The Comeback Trail

Similar in 82%

The Crew (2000)

Plot Summary:

Four retired mobsters plan one last crime to save their retirement home.

Similar in 78%

The Freshman (1990)

Plot Summary:

Clark Kellogg is a young man starting his first year at film school in New York City. After a small time crook steals all his belongings, Clark meets Carmine "Jimmy the Toucan" Sabatini, an "importer" bearing a startling resemblance to a certain cinematic godfather. When Sabatini makes Clark an offer he can't refuse, he finds himself caught up in a caper involving endangered species and fine dining.

Similar in 80%

The Jerky Boys (1995)

Plot Summary:

When two unemployed telephone pranksters decide to use their vocal "talents" to impersonate a Chicago mob boss and curry favor with organized crime in New York, the trouble begins. It isn't long before Johnny and Kamal (the "Jerky Boys" of crank call fame) are wanted by the local mafia, the police, and their neighbor.

Similar in 90%

We're Talkin' Serious Money (1992)

Plot Summary:

A couple of bumbling con men go on the lam when they can't repay a loan from the mob.

Similar in 76%

Queenpins (2021)

Plot Summary:

Bored and frustrated suburban homemaker Connie and her best pal JoJo, a vlogger with dreams, turn a hobby into a multi-million-dollar counterfeit coupon caper. After firing off a letter to the conglomerate behind a box of cereal gone stale, and receiving an apology along with dozens of freebies, the duo hatch an illegal coupon club scheme that scams millions from mega-corporations and delivers deals to legions of fellow coupon clippers. On the trail to total coupon dominance, a hapless Loss Prevention Officer from the local supermarket chain joins forces with a determined U.S. Postal Inspector in hot pursuit of these newly minted “Queenpins” of pink collar crime.

Similar in 76%

Stir Crazy (1980)

Plot Summary:

New Yorkers, Skip Donahue and Harry Monroe, have no jobs and no prospects. They decide to flee the city and find work elsewhere, and land jobs as woodpeckers to promote the opening of a bank. When their feathery costumes are stolen and used in a bank robbery, they no longer have to worry about employment -- they're sent to prison!.

Similar in 82%

We're No Angels (1989)

Plot Summary:

Two escaped cons only prayer to escape is to pass themselves off as priests and pass by the police blockade at the border into the safety of Canada.

Similar in 79%

Analyze This (1999)

Plot Summary:

Countless wiseguy films are spoofed in this film that centers on the neuroses and angst of a powerful Mafia racketeer who suffers from panic attacks. When Paul Vitti needs help dealing with his role in the "family," unlucky shrink Dr. Ben Sobel is given just days to resolve Vitti's emotional crisis and turn him into a happy, well-adjusted gangster.

Similar in 90%

Analyze That (2002)

Plot Summary:

The mafia's Paul Vitti is back in prison and will need some serious counseling when he gets out. Naturally, he returns to his analyst Dr. Ben Sobel for help and finds that Sobel needs some serious help himself as he has inherited the family practice, as well as an excess stock of stress.

Similar in 75%

The Big Bounce (2004)

Plot Summary:

A small-time con artist and a Hawaiian real estate developer's mischievous, enterprising mistress team up for a potential $200,000 score.

Similar in 90%

Screwed (2000)

Plot Summary:

A chauffeur kidnaps his rich boss's dog to hold it for ransom, but when she accidentally gets the dog back, she thinks that it's the chauffeur who's been kidnapped.

Similar in 86%

Man of the House (2005)

Plot Summary:

Texas Ranger Roland Sharp is assigned to protect the only witnesses to the murder of a key figure in the prosecution of a drug kingpin -- a group of University of Texas cheerleaders. Sharp must now go undercover as an assistant cheerleading coach and move in with the young women.

Similar in 78%

Nuns on the Run (1990)

Plot Summary:

Brian and Charlie work for a gangster. When the boss learns they want to "leave" he sets them up to be killed, after they help rob the local Triads of their drug dealing profits. B&C decide to steal the money for themselves, but when their escape doesn't go to plan, they have to seek refuge in a Nuns' teacher training school.

Similar in 83%

Fun with Dick and Jane (2005)

Plot Summary:

After Dick Harper loses his job at Globodyne in an Enron-esque collapse, he and his wife, Jane, turn to crime in order to handle the massive debt they now face. Two intelligent people, Dick and Jane actually get pretty good at robbing people and even enjoy it -- but they have second thoughts when they're reminded that crime can hurt innocent people. When the couple hears that Globodyne boss Jack McCallister actually swindled the company, they plot revenge.

Similar in 81%

Wise Guys (1986)

Plot Summary:

Harry Valentini and Moe Dickstein are both errand boys for the Mob. When they lose $250,000, they are set up to kill each other. But they run off to Atlantic City and comedy follows.

Similar in 75%

Midnight Run (1988)

Plot Summary:

An accountant embezzles $15 million of mob money, jumps bail and is chased by bounty hunters, the FBI, and the Mafia.

Similar in 83%

Ruby & Quentin (2003)

Plot Summary:

After hiding his loot and getting thrown in jail, Ruby, a brooding outlaw encounters Quentin, a dim-witted and garrulous giant who befriends him. After Quentin botches a solo escape attempt, they make a break together. Unable to shake the clumsy Quentin Ruby is forced to take him along as he pursues his former partners in crime to avenge the death of the woman he loved and get to the money.

Similar in 78%

Bullets Over Broadway (1994)

Plot Summary:

Set in 1920's New York City, this movie tells the story of idealistic young playwright David Shayne. Producer Julian Marx finally finds funding for the project from gangster Nick Valenti. The catch is that Nick's girl friend Olive Neal gets the part of a psychiatrist, and Olive is a bimbo who could never pass for a psychiatrist as well as being a dreadful actress. Agreeing to this first compromise is the first step to Broadway's complete seduction of David, who neglects longtime girl friend Ellen. Meanwhile David puts up with Warner Purcell, the leading man who is a compulsive eater, Helen Sinclair, the grand dame who wants her part jazzed up, and Cheech, Olive's interfering hitman / bodyguard. Eventually, the playwright must decide whether art or life is more important.

Similar in 78%

Get Shorty (1995)

Plot Summary:

Chili Palmer is a Miami mobster who gets sent by his boss, the psychopathic "Bones" Barboni, to collect a bad debt from Harry Zimm, a Hollywood producer who specializes in cheesy horror films. When Chili meets Harry's leading lady, the romantic sparks fly. After pitching his own life story as a movie idea, Chili learns that being a mobster and being a Hollywood producer really aren't all that different.

Similar in 83%

The Whole Nine Yards (2000)

Plot Summary:

A mobster named Jimmy the Tulip agrees to cooperate with an FBI investigation in order to stay out of prison; he's relocated by the authorities to a life of suburban anonymity as part of a witness protection program. It's not long before a couple of his new neighbors figure out his true identity and come knocking to see if he'd be up for one more hit, suburban style.

Similar in 76%

Last Vegas (2013)

Plot Summary:

Three sixty-something friends take a break from their day-to-day lives to throw a bachelor party in Las Vegas for their last remaining single pal.

Similar in 82%

The Bucket List (2007)

Plot Summary:

Corporate billionaire Edward Cole and working class mechanic Carter Chambers are worlds apart. At a crossroads in their lives, they share a hospital room and discover they have two things in common: a desire to spend the time they have left doing everything they ever wanted to do and an unrealized need to come to terms with who they are. Together they embark on the road trip of a lifetime, becoming friends along the way and learning to live life to the fullest, with insight and humor.