20 movies like The Boss, ordered by similarity : Get Hard(2015), The Old Man & the Gun(2018), Pardon Us(1931), Hannibal Brooks(1969), The Big Job(1965), Up the River(1930), Papillon(2017), City Island(2009), Barbershop: The Next Cut(2016), Apprentice(2016), Guardians of the Galaxy Vol. 2(2017), Transamerica(2005) ...
Comedy
USA
2016
99 Minutes
Melissa McCarthy Kristen Bell Peter Dinklage Ella Anderson Tyler Labine Kathy Bates Cecily Strong Mary Sohn Kristen Schaal Eva Peterson Timothy Simons
mogul prisoner assistant parent young girl brash cheeky hilarious arena prison apartment office street car arrest prison egoism redemption hope money
A titan of industry is sent to prison after she's caught insider trading. When she emerges ready to rebrand herself as America's latest sweetheart, not everyone she screwed over is so quick to forgive and forget.
Comedy
USA
2015
99 Minutes
Will Ferrell Kevin Hart Craig T. Nelson Alison Brie Edwina Findley Ariana Neal Erick Chavarria Tip "T.I." Harris Paul Ben-Victor Jon Eyez Nito Larioza
wealthy man criminal judge businessman prison guard prisoner amusing cheeky hilarious courtroom car ghetto house street park fraud prison survival courage life
When millionaire James King is jailed for fraud and bound for San Quentin, he turns to Darnell Lewis to prep him to go behind bars.
Comedy, Mystery & Thriller, Drama
USA|UK
2018
93 Minutes
Robert Redford Casey Affleck Sissy Spacek Danny Glover Tom Waits Tika Sumpter Ari Elizabeth Johnson Teagan Johnson Gene Jones John David Washington Barlow Jacobs
prisoner prison guard bank robber wife detective escape artist amusing gutsy bleak suspenseful tense california san quentin penitentiary prison bank car escape bank heist life story prison
Based on the true story of Forrest Tucker and his audacious escape from San Quentin at the age of 70 to an unprecedented string of heists that confounded authorities and enchanted the public.
Comedy
USA
1931
55 Minutes
bootlegger partner warden daughter cellmate prisoner playful madcap prison office cell school field dentist's office prison life prison break prohibition impersonation friendship escape
Two guys end up in prison after attempting to sell beer to a policeman during Prohibition.
Comedy, War, Drama
UK|USA
1969
101 Minutes
Oliver Reed Michael J. Pollard Karin Baal Wolfgang Preiss Helmut Lohner Peter Carsten
prisoner of war soldier englishman elephant escaped convict zookeeper charming cheeky confident endearing fascinating incredible prison camp private zoo alps munich mountain war zone world war ii prison break
A prisoner of war working at a zoo gets the chance to escape from the Germans, so he does and he takes with him the elephant that he's been caring for. Together they head for the Swiss border and freedom.
Comedy
UK
1965
88 Minutes
Sidney James Sylvia Syms Dick Emery Lance Percival Joan Sims Jim Dale Edina Ronay Deryck Guyier Brian Rawlinson Reginald Beckwith David Horne
bank robbers prisoner police captain girlfriend airy amusing hilarious charming prison police station bank bank robbery life after prison prison release money love rise revenge quest adventure
An inept gang of bank robbers, led by George The Brain, are caught and sentenced to 15 years hard labour each. When they are released from prison they start out to collect the money they ... See full summary »
Comedy
USA
1930
90 Minutes
Spencer Tracy Humphrey Bogart Warren Hymer Claire Luce
prisoner partner inmate parolee ex-boyfriend love interest cheeky lighthearted amusing prison town mission street cell prison break friendship prison life blackmail baseball framed
When paroled trustee Steve and former inmate Judy who try to put their criminal lives behind them are blackmailed, two career criminals come to their rescue.
Adventure, History, Biography, Drama
USA|Czech Republic|Spain
2017
133 Minutes
Charlie Hunnam Rami Malek Roland Møller Nina Senicar Tommy J. Flanagan Eve Hewson Christopher Fairbank Brian Vernel
convict innocent man prison guard prisoner escape artist friend tense bleak thrilling suspenseful incredible intricate prison island prison cell paris french guiana apartment prison prison break
Wrongfully convicted for murder, Henri Charriere forms an unlikely relationship with fellow inmate and quirky convicted counterfeiter Louis Dega, in an attempt to escape from the notorious penal colony on Devil's Island.
Comedy
USA
2009
103 Minutes
Andy Garcia Julianna Margulies Steven Strait Emily Mortimer Ezra Miller Dominik García-Lorido Carrie Baker Reynolds Hope Glendon-Ross Alan Arkin Louis Mustillo Jee Young Han
prison guard ex-convict wife daughter father son hilarious touching bronx, n.y. prison audition school family home island family forgiveness father/son relationship responsibility love new life
Prison guard Vince tells Molly from acting class, that one inmate is his 24 y.o. love child. Vince takes him home to stay with his family - straight A son with fat girl fetish, college dropout/stripper daughter and cute wife.
Comedy
USA
2016
112 Minutes
Ice Cube Cedric Kyles Regina Hall Sean Patrick Thomas Eve Anthony Anderson Jazsmin Lewis JB Smoove Common Nicki Minaj Lamorne Morris
barber stylist co-worker client son gang member cheeky emotional creative barbershop apartment street bar car police station hard times bonding gangs conversation neighborhood watch
As their surrounding community has taken a turn for the worse, the crew at Calvin's Barbershop come together to bring some much needed change to their neighborhood.
Drama
Singapore|Germany|France|Hong Kong|Qatar
2016
96 Minutes
Firdaus Rahman Wan Hanafisu Mastura Ahmad Boon Pin Koh Nickson Cheng Crispian Chan Gerald Chew
prison guard prisoner executioner apprentice sister father brooding emotional intense prison apartment execution chamber market car street prison execution guilt anger acceptance
Inevitably, a transfer to a maximum security prison will eventually challenge the integrity and ethics of a young correctional officer on his way to become a chief executioner.
Sci-Fi, Adventure, Comedy, Action, Fantasy
USA
2017
135 Minutes
Chris Pratt Zoe Saldana Dave Bautista Michael Rooker Karen Gillan Sylvester Stallone Pom Klementieff Kurt Russell Elizabeth Debicki Tommy J. Flanagan Chris Sullivan
adventurer bounty hunter villain raccoon humanoid father brash cheeky confident thrilling offbeat hilarious space spaceship colony alien planet prison outer space team misfits
The Guardians struggle to keep together as a team while dealing with their personal family issues, notably Star-Lord's encounter with his father the ambitious celestial being Ego.
Gay & Lesbian, Comedy, Drama
USA
2005
103 Minutes
Felicity Huffman Kevin Zegers Fionnula Flanagan Graham Greene Burt Young Elizabeth Peña Bianca Leigh Jon Budinoff Carrie Preston Maurice Orozco
transsexual son rancher mother therapist emotional uplifting positive los angeles new york city prison phoenix car road trip father/son relationship car theft sexual abuse sex change sexual identity transformation
A preoperative transgender woman takes an unexpected journey when she learns that she fathered a son, now a teenage runaway hustling on the streets of New York.
Comedy, Fantasy
2019
109 Minutes
Regina Hall Issa Rae Marsai Martin Justin Hartley Tracee Ellis Ross Tone Bell Mikey Day JD McCrary Tucker Meek Thalia Tran Marley Taylor
co-worker media mogul assistant employee teenager amusing brash hilarious outlandish unrestrained school apartment office physical transformation role reversal friendship career transformation adventure discovery
Jordan is a take-no-prisoners mogul who torments her long-suffering assistant and employees on a daily basis. She soon faces an unexpected threat to her personal life and career when she magically transforms into a 13-year-old version of herself.
Mystery & Thriller, Comedy, Action, Drama
USA
2010
108 Minutes
Keanu Reeves James Caan Vera Farmiga Judy Greer Peter Stormare Fisher Stevens Bill Duke Currie Graham David Costabile Danny Hoch
bank robber actress prisoner ex-wife thief woman amusing charming witty lighthearted melodramatic emotional united states prison bank bank robbery love love interest money prison
Released from prison for a crime he didn't commit, an ex-con targets the same bank he was sent away for robbing.
Drama
2017
106 Minutes
Jean Jean Ramón Emilio Candelario Judith Rodriguez Jose Cruz Manuel Raposo Karina Valdez Aleja Johnson Carlota Carretero Keunis Álvarez Orestes Amador
prison guard prisoner prisoners messenger gangsters love interest romantic interest romantic rival rival dark disturbing emotional engaging gripping intense moving passionate powerful raw tense
Incarcerated in the Dominican Republic, an inmate uses sign language to communicate with his imprisoned girlfriend at an adjacent institution.
Comedy
UK
1960
87 Minutes
Peter Sellers Wilfrid Hyde-White David Lodge Bernard Cribbins Maurice Denham Lionel Jeffries Irene Handl Liz Fraser Beryl Reid Noel Hood Myrette Morven
inmate accomplice cellmate prison official con artist witty endearing lighthearted england prison sewer jewelry theft prison life prison break impersonation alibi adventure temptation 1960s
Dodger Lane (Peter Sellers) has planned the perfect robbery while in prison. He intends to break out of prison, steal a fortune in diamonds, and break back into prison before anyone notices... See full summary »
Comedy, Drama
USA
2017
82 Minutes
Menashe Lustig Ruben Niborski Yoel Weisshaus Meyer Schwartz Yoel Falkowitz Mirka Hermoza Laznik Abraham Bresky Jorge Cea
hasidic jew grocer father son widower emotional moving spirited tender new york city grocery store house park cemetery temple judaism single parents single life parent/child relationship love
Within Brooklyn's ultra-orthodox Jewish community, a widower battles for custody of his son. A tender drama performed entirely in Yiddish, the film intimately explores the nature of faith and the price of parenthood.
Romance, Comedy, Drama
USA
2016
118 Minutes
Jennifer Aniston Kate Hudson Julia Roberts Jason Sudeikis Britt Robertson Timothy Olyphant Héctor Elizondo Jack Whitehall Jennifer Garner Aasif Mandvi Sarah Chalke
single mother ex-husband son friend widower career woman cheeky emotional gripping amusing heartwarming house street gym school car store motherhood stress holidays
Three generations come together in the week leading up to Mother's Day.
Comedy, Action
USA
1982
97 Minutes
Nick Nolte Eddie Murphy Annette O'Toole Frank McRae James Remar David Patrick Kelly Sonny Landham Brion James Kerry Sherman Jonathan Banks James Keane
police officer prisoner bank robber henchman girlfriend confident raw san francisco country road prison bar police station apartment crime murder robbery investigation culture clash mystery pursuit
A hard-nosed cop reluctantly teams up with a wise-cracking criminal temporarily paroled to him, in order to track down a killer.
Comedy, Crime, Drama
USA|China
2017
119 Minutes
Channing Tatum Adam Driver Farrah Mackenzie Riley Keough Daniel Craig Katie Holmes Charles Halford Seth MacFarlane Jack Quaid Brian Gleeson Katherine Waterston
brother friend robber prisoner construction worker bank robber amusing brooding confident gripping madcap west virginia prison dump racetrack heist nascar hard times family honor bad luck
Two brothers attempt to pull off a heist during a NASCAR race in North Carolina.