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Movies Like The Boss

For those captivated by The Boss, should consider this hand-picked list which questions the purpose and weight of our choices all while offering targets the intellect with complex, multi-layered ideas. Carefully balances character depth with narrative flow makes this definitely worth a watch.

Mood Breakdown
Runtime Cluster

Standard feature-length experiences.

Viewer Fit

Best for fans of who appreciate concise storytelling.

Top Picks

Casino Jack
5.8

Casino Jack

2010

Based on a true story, a hot shot Washington DC lobbyist and his protégé go down hard as their schemes to peddle influence lead to corruption and murder.

Married to the Mob
6.0

Married to the Mob

1988

Angela de Marco is fed up with her gangster husband's line of work and wants no part of the crime world. When her husband is killed for having an affair with the mistress of mob boss Tony "The Tiger" Russo, Angela and her son depart for New York City to make a fresh start. Unfortunately, Tony has set his sights upon Angela -- and so has an undercover FBI agent looking to use her to bust Tony.

Veronica Mars
6.6

Veronica Mars

2014

Years after walking away from her past as a teenage private eye, Veronica Mars gets pulled back to her hometown - just in time for her high school reunion - in order to help her old flame Logan Echolls, who's embroiled in a murder mystery.

Jackass Presents: Bad Grandpa
6.1

Jackass Presents: Bad Grandpa

2013

86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.

The Stöned Age
5.9

The Stöned Age

1994

Determined to avoid another night of driving aimlessly around Torrance in the Blue Torpedo, Joe and Hubbs set out on a quest for fine chicks. Their paths soon cross with Tack, from whom they learn about a pair of foreign radical chicks hanging out near the Frankie Avalon place. Over Joe's objections, Hubbs worms Tack out of the deal, and the pair take a slow ride toward their destiny.

The Joneses
6.2

The Joneses

2010

A seemingly perfect family moves into a suburban neighborhood, but when it comes to the truth as to why they're living there, they don't exactly come clean with their neighbors.

The Duchess and the Dirtwater Fox
6.1

The Duchess and the Dirtwater Fox

1976

A female hustler is chasing after rich men, but becomes repeatedly mixed up with a suave con man and card shark through a series of misadventures before falling in love with him.

Analyze That
5.8

Analyze That

2002

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.

More Movies Like The Boss

The Ladykillers
6.1

The Ladykillers

2004

An eccentric, if not charming Southern professor and his crew pose as a band in order to rob a casino, all under the nose of his unsuspecting landlord – a sharp old woman.

Clerks III
6.0

Clerks III

2022

After narrowly surviving a massive heart attack, Randal enlists his old friend Dante to help him make a movie immortalizing their youthful days at the little convenience store that started it all.

The Disaster Artist
7.1

The Disaster Artist

2017

An aspiring actor in Hollywood meets an enigmatic stranger by the name of Tommy Wiseau, the meeting leads the actor down a path nobody could have predicted; creating the worst movie ever made.

Fired Up!
6.1

Fired Up!

2009

Popular high schoolers and best friends Shawn and Nick decide to ditch football camp for cheerleader camp. For the girls and for the glory.

The Hustle
6.2

The Hustle

2019

Two female scam artists, one low rent and the other high class, compete to swindle a naïve tech prodigy out of his fortune. A remake of the 1988 comedy "Dirty Rotten Scoundrels."

The Silencers
6.0

The Silencers

1966

Matt Helm is called out of retirement to stop the evil Big O organization who plan to explode an atomic bomb over Alamagordo, NM, and start WW III.

Horrible Bosses
6.6

Horrible Bosses

2011

For Nick, Kurt and Dale, the only thing that would make the daily grind more tolerable would be to grind their intolerable bosses into dust. Quitting is not an option, so, with the benefit of a few-too-many drinks and some dubious advice from a hustling ex-con, the three friends devise a convoluted and seemingly foolproof plan to rid themselves of their respective employers... permanently.

10 Items or Less
6.2

10 Items or Less

2006

An actor who is considering the role of a supermarket manager arrives at a grocery store on the outskirts of Los Angeles to do some field research. He subsequently becomes stranded, without a car or cell phone, and accepts a ride home with Scarlet, a cashier who is about to interview for a new job. The actor rediscovers the essence of his craft while helping Scarlet gain the confidence she needs to change her life.

Death to Smoochy
5.9

Death to Smoochy

2002

Tells the story of Rainbow Randolph, the corrupt, costumed star of a popular children's TV show, who is fired over a bribery scandal and replaced by squeaky-clean Smoochy, a puffy fuchsia rhinoceros. As Smoochy catapults to fame - scoring hit ratings and the affections of a network executive - Randolph makes the unsuspecting rhino the target of his numerous outrageous attempts to exact revenge and reclaim his status as America's sweetheart.

Extract
5.8

Extract

2009

The owner of a factory that produces flavor extracts, Joel Reynold seems to have it all, but really doesn't. What's missing is sexual attention from his wife, Suzie. Joel hatches a convoluted plan to get Suzie to cheat on him, thereby clearing the way for Joel to have an affair with Cindy, an employee. But what Joel doesn't know is that Cindy is a sociopathic con artist, and a freak workplace accident clears the way for her to ruin Joel forever.

Barb & Star Go to Vista Del Mar
6.0

Barb & Star Go to Vista Del Mar

2021

The story of best friends Barb and Star, who leave their small midwestern town for the first time to go on vacation in Vista Del Mar, Florida, where they soon find themselves tangled up in adventure, love, and a villain’s evil plot to kill everyone in town.

Taking Care of Business
6.3

Taking Care of Business

1990

An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.

Why These Movies Are Similar

These recommendations share core qualities with The Boss (2016): Comedy 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 The Boss.

See full details for The Boss (2016)

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