3 Movies Like Tommy Boy (1995)

Staff & contributors
At first glance, The Madness of King George seemed like a history lesson about King George III. Like plenty of British royalty dramas, the film has all the opulent trappings in its sets and costumes, as well as some of the best actors from the British isles. However, unlike other depictions of the monarchy, the film depicts the king not as a benevolent ruler or oppressive tyrant– instead, King George III is terribly human, with his memory failing, being unsettled by loss, and concern over his health, which involves having to look at his urine. But the historical satire, based on the 1991 stage play, still manages to have the same mockery towards the opportunistic court, while still retaining sympathy for the very nobility it mocks, through original playwright Alan Bennett’s adept writing, as well as the excellent performance of the stacked ensemble cast.

Genre: Comedy, Drama, History

Actor: Adrian Scarborough, Alan Bennett, Amanda Donohoe, Anthony Calf, Barry Stanton, Caroline Harker, Charlotte Curley, Clive Brunt, Colin McPhillamy, Cyril Shaps, David Leon, Dermot Keaney, Geoffrey Palmer, Helen Mirren, Iain Mitchell, Ian Holm, Janine Duvitski, Jeremy Child, Jim Carter, Joanna Hall, John Wood, Julian Rhind-Tutt, Julian Wadham, Michael Grandage, Nicholas Irons, Nicholas Selby, Nick Sampson, Nigel Hawthorne, Paul Corrigan, Peter Woodthorpe, Robert Swann, Roger Ashton-Griffiths, Roger Hammond, Rupert Everett, Rupert Graves, Selina Cadell, Struan Rodger

Director: Nicholas Hytner

Rating: PG-13

Before “burnout,” “bullshit jobs,” and “quiet quitting” became part of our everyday lexicon, there was a film in the ‘90s that prophesied the rise of these workplace problems. Office Space follows three co-workers who, having had enough of their dreary low-paying jobs, fight back against their company via an embezzlement scheme. 

Office Space makes the most out of its indie budget as it mostly takes place in the cramped quarters of a company, effectively bottling us into the cubicled windowless world of the characters. But the real beauty of the film is in the details, from its quick zingers and thoughtful takes on the essence of work down to its elaborate “planning to plan” scheme in the background and the employees’ forced politeness singing happy birthday to their boss. Modern viewers will notice that Office Space sits right in between the dystopian thriller Severance and the beloved sitcom The Office—a dark comedy that highlights the necessity of humanity in everyday work. 

Genre: Comedy, Drama

Actor: Ajay Naidu, Alexandra Wentworth, Ali Wentworth, Barbara George-Reiss, Cassie Townsend, Charissa Allen, David Herman, Diedrich Bader, Gabriel Folse, Gary Cole, Greg Pitts, Heath Young, Jack Betts, Jackie Belvin, Jennifer Aniston, Jennifer Jane Emerson, Jesse De Luna, Joe Bays, John C. McGinley, Josh Bond, Justin Possenti, K. Todd Lytle, Kinna McInroe, Kyle Scott Jackson, Linda Wakeman, Michael McShane, Mike Judge, Orlando Jones, Paul Willson, R.C. Keene, Richard Riehle, Ron Livingston, Rupert Reyes, Samantha Inoue Harte, Spencer Kayden, Stephen Root, Todd Duffey, Tom Schuster

Director: Mike Judge

Rating: R

Not enough movies tell the stories of the down-on-luck, kind of uncool wolf-pack that still goes out into town with their wallets on chains hanging from their pockets and try their luck with the ladies. Mike, heart-broken actor-comedian pines over his ex long after she's been gone, while his guys - Trent, Rob and Sue - try to help him get back in the game in a series of nights club-hopping and wingman-ing. You find yourself empathizing with Mike almost immediately if you've ever had a broken heart and root for him throughout his highs and fairly embarrassing lows. Sprinkled with clever references and subtle, refreshing humor, Mike's journey to find closure is more than likely to warm your heart.

As a bonus, the flawed yet endearing gang of twenty-something struggling actors will take you to that charming 90's nightlife in Los Angeles (with music to die for, by the way) and remind you that boys will be boys and that they're just doing their best helping each other and themselves to keep it together with lots of "You're so money, and you don't even know it!".

Genre: Comedy, Drama

Actor: Ahmed Ahmed, Alex Désert, Alex Désert, Bernard Serrano, Blake Lindsley, Brooke Langton, Curtis Lindersmith, Deena Martin, Heather Graham, Jan Dykstra, Jessica Buchman, Joan Favreau, Jon Favreau, Katherine Kendall, Kevin James Kelly, Maddie Corman, Martina Migenes, Molly Stern, Pamela Shaw, Patrick Van Horn, Rio Hackford, Ron Livingston, Samantha Lemole, Stephanie Ittleson, Stephen Gaghan, Vernon Vaughn, Vince Vaughn

Director: Doug Liman

Rating: R