Labor Day Movies
by blockbuster-rewind | created - 1 month ago | updated - 1 month ago | Public- Instant Watch Options
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1. Office Space (1999)
R | 89 min | Comedy
Three company workers who hate their jobs decide to rebel against their greedy boss.
Director: Mike Judge | Stars: Ron Livingston, Jennifer Aniston, David Herman, Ajay Naidu
Votes: 287,650 | Gross: $10.82M
This is perhaps the MOST classic of work movies. I wonder if they had any clue they were making such a classic film when they were making the movie.
2. Horrible Bosses (2011)
R | 98 min | Comedy, Crime
Three friends conspire to murder their awful bosses when they realize they are standing in the way of their happiness.
Director: Seth Gordon | Stars: Jason Bateman, Charlie Day, Jason Sudeikis, Steve Wiebe
Votes: 469,745 | Gross: $117.54M
Wow! Jennifer Aniston manages to nab two of the top Labor Day movies.! ;-) Another trend is Kevin Spacey as a really unlikable jerk-of-a-boss. He's on this list several times.
3. Glengarry Glen Ross (1992)
R | 100 min | Crime, Drama, Mystery
An examination of the machinations behind the scenes at a real estate office.
Director: James Foley | Stars: Al Pacino, Jack Lemmon, Alec Baldwin, Alan Arkin
Votes: 116,253 | Gross: $10.73M
This has an all-star cast with every single actor delivering a top-notch performance! Features Kevin Spacey as another unlikable boss on this movie list, not to mention Ed Harris, Al Pacino, Alec Baldwin, and Jack Lemmon, among others.
4. Clerks (1994)
R | 92 min | Comedy
A day in the lives of two convenience clerks named Dante and Randal as they annoy customers, discuss movies, and play hockey on the store roof.
Director: Kevin Smith | Stars: Brian O'Halloran, Jeff Anderson, Marilyn Ghigliotti, Lisa Spoonauer
Votes: 232,382 | Gross: $3.15M
Kind of low-budget, but very entertaining and easy-to-relate-to for any working class schlub like myself. ;-) I especially like the down-to-earth, and often too-frank conversations the characters have throughout the movie.
5. The Company Men (2010)
R | 104 min | Drama
The story centers on a year in the life of three men trying to survive a round of corporate downsizing at a major company - and how that affects them, their families, and their communities.
Director: John Wells | Stars: Ben Affleck, Chris Cooper, Tommy Lee Jones, Suzanne Rico
Votes: 48,227 | Gross: $4.44M
This shows the serious side of downsizing. A very real film for far too many people in this recent economy.
6. Erin Brockovich (2000)
R | 131 min | Biography, Drama
An unemployed single mother becomes a legal assistant and almost single-handedly brings down a California power company accused of polluting a city's water supply.
Director: Steven Soderbergh | Stars: Julia Roberts, Albert Finney, David Brisbin, Dawn Didawick
Votes: 221,392 | Gross: $125.60M
Julia Roberts shows she can really act with this film. And Aaron Eckhart gets a chance to show his acting chops, too.
7. Nine to Five (1980)
PG | 109 min | Comedy
Three female employees of a sexist, egotistical, lying, hypocritical bigot find a way to turn the tables on him.
Director: Colin Higgins | Stars: Jane Fonda, Lily Tomlin, Dolly Parton, Dabney Coleman
Votes: 39,428 | Gross: $103.29M
Even the theme song by Dolly Parton is sort-of a classic, blue collar song.
8. Outsourced (2006)
PG-13 | 103 min | Comedy, Drama, Romance
After his entire department is outsourced, an American novelty products salesman (Hamilton) heads to India to train his replacement.
Director: John Jeffcoat | Stars: Josh Hamilton, Ayesha Dharker, Asif Basra, Matt Smith
Votes: 12,195 | Gross: $0.16M
I thoroughly enjoyed the televison series based upon this foreign film, but was disappointed that it was cancelled after only one spectacular season.
9. Swimming with Sharks (1994)
R | 93 min | Comedy, Crime
A young, naive Hollywood studio assistant finally turns the tables on his incredibly abusive producer boss.
Director: George Huang | Stars: Kevin Spacey, Frank Whaley, Michelle Forbes, Benicio Del Toro
Votes: 25,019 | Gross: $0.38M
Here's another stellar appearance by Kevin Spacey as a boss from hell.
10. Trading Places (1983)
R | 116 min | Comedy
A snobbish investor and a wily street con artist find their positions reversed as part of a bet by two callous millionaires.
Director: John Landis | Stars: Eddie Murphy, Dan Aykroyd, Ralph Bellamy, Don Ameche
Votes: 165,825 | Gross: $90.40M
Not only is this a great Labor Day movie, but it's a great Christmas movie, a great comedy, and simply a great movie... period.
11. The Firm (1993)
R | 154 min | Drama, Mystery, Thriller
A young lawyer joins a prestigious law firm only to discover that it has a sinister dark side.
Director: Sydney Pollack | Stars: Tom Cruise, Jeanne Tripplehorn, Gene Hackman, Hal Holbrook
Votes: 147,731 | Gross: $158.35M
This one's a bit hokey at times, but it's still an entertaining workplace film, featuring some of my favorite actors, such as Tom Cruise, Gene Hackman, Ed Harris, and Wilford Brimley.
12. Silkwood (1983)
R | 131 min | Biography, Drama, History
A worker at a plutonium processing plant is purposefully contaminated, psychologically tortured and possibly murdered to prevent her from exposing worker safety violations at the plant.
Director: Mike Nichols | Stars: Meryl Streep, Kurt Russell, Cher, Craig T. Nelson
Votes: 22,206 | Gross: $35.62M
It's a bit of a chick flick, but it's also intriguing the first time around. And Meryl Streep is a great actress in almost anything she does.
13. Norma Rae (1979)
PG | 114 min | Drama
A young single mother and textile worker agrees to help unionize her mill despite the problems and dangers involved.
Director: Martin Ritt | Stars: Sally Field, Beau Bridges, Ron Leibman, Pat Hingle
Votes: 12,840 | Gross: $22.23M
Another chick flick, but I think Sally Field won an Academy Award for her performance in this.
14. The Hudsucker Proxy (1994)
PG | 111 min | Comedy, Drama, Fantasy
A naive business graduate is installed as president of a manufacturing company as part of a stock scam.
Directors: Joel Coen, Ethan Coen | Stars: Tim Robbins, Paul Newman, Jennifer Jason Leigh, Charles Durning
Votes: 85,092 | Gross: $2.87M
The old-timey performances take a little getting used to, but in the end it's a very funny movie.
15. Tootsie (1982)
PG | 116 min | Comedy, Drama, Romance
Michael Dorsey, an unsuccessful actor, disguises himself as a woman in order to get a role on a trashy hospital soap.
Director: Sydney Pollack | Stars: Dustin Hoffman, Jessica Lange, Teri Garr, Dabney Coleman
Votes: 114,692 | Gross: $177.20M
I read the script for this in college, and most of my classmates agreed that it's amazing that this turned out to be a great movie (and probably proof of the genius of Sydney Pollack), since it was rather dry on paper. It's also a testament to a good cast of actors.
16. Boiler Room (2000)
R | 120 min | Crime, Drama, Thriller
A college dropout, attempting to live up to his father's high standards, gets a job as a broker for a suburban investment firm which puts him on the fast track to success. But the job might not be as legitimate as it first appeared to be.
Director: Ben Younger | Stars: Giovanni Ribisi, Vin Diesel, Nia Long, Nicky Katt
Votes: 56,455 | Gross: $16.94M
This was more of a sleeper hit when it was released, but it has a clever script with spectacular performances by several of the principal actors, especially Giovanni Rabisi. And it's one of the few films Vin Diesel can actually be proud of having participated in (the other being Saving Private Ryan, in which Rabisi also appeared).
17. Up in the Air (I) (2009)
R | 109 min | Comedy, Drama, Romance
Ryan's job is to travel around the country firing off people. When his boss hires Natalie, who proposes firing people via video conference, he tries to convince her that her method is a mistake.
Director: Jason Reitman | Stars: George Clooney, Vera Farmiga, Anna Kendrick, Jason Bateman
Votes: 349,401 | Gross: $83.82M
Like The Company Men, this is another film showing the harsh side of being on the negative end of job loss, but it still manages to be sympathetic to the hatchet man.
18. Flash of Genius (2008)
PG-13 | 119 min | Biography, Drama
Robert Kearns takes on the Detroit automakers who he claims stole his idea for the intermittent windshield wiper.
Director: Marc Abraham | Stars: Greg Kinnear, Lauren Graham, Alan Alda, Tim Eddis
Votes: 17,821 | Gross: $4.23M
I always like Greg Kinnear. This is the first of two films on this list about the huge Ford corporation taking advantage of Labor. But judging by the fact that they apparently particpated in these films at least by allowing their logo to be used, I guess they've come to the conclusion that some of their past policies and behaviors were wrong.
19. The Proposal (I) (2009)
PG-13 | 108 min | Comedy, Drama, Romance
A pushy boss forces her young assistant to marry her in order to keep her visa status in the U.S. and avoid deportation to Canada.
Director: Anne Fletcher | Stars: Sandra Bullock, Ryan Reynolds, Mary Steenburgen, Craig T. Nelson
Votes: 360,403 | Gross: $163.96M
My wife absolutley loves this film! I'm just a casual fan, but freely admit it's an entertaining comedy.
20. Sunshine Cleaning (2008)
R | 91 min | Comedy, Drama
In order to raise the tuition to send her young son to private school, a mom starts an unusual business -- a biohazard removal/crime scene clean-up service -- with her unreliable sister.
Director: Christine Jeffs | Stars: Amy Adams, Emily Blunt, Alan Arkin, Jason Spevack
Votes: 74,135 | Gross: $12.06M
I was pleasantly surprised by the quirky story in this movie.
21. The Good Girl (2002)
R | 93 min | Drama, Romance
A discount store clerk strikes up an affair with a stock boy who considers himself the incarnation of Holden Caulfield.
Director: Miguel Arteta | Stars: Jennifer Aniston, Jake Gyllenhaal, Deborah Rush, Mike White
Votes: 47,436 | Gross: $14.02M
Whoa, Jennifer Anniston making yet another appearance on the list of best Labor Day films! This one's a serious performance by her, although the movie still has it's share of black humor in it.
22. Philadelphia (1993)
PG-13 | 125 min | Drama
When a man with HIV is fired by his law firm because of his condition, he hires a homophobic small time lawyer as the only willing advocate for a wrongful dismissal suit.
Director: Jonathan Demme | Stars: Tom Hanks, Denzel Washington, Roberta Maxwell, Buzz Kilman
Votes: 258,120 | Gross: $77.32M
I always thought this movie was over-rated, but it definitely qualifies as a good Labor Day movie. I think too often in this film Tom Hanks just looks blankly at the camera and allows the audience to project their own emotions onto his plain expression. Normally I really like Tom Hanks and Denzel Washington, and although this is still a decent film, the quality is a bit exaggerated.
23. North Country (2005)
R | 126 min | Drama
A fictionalized account of the first major successful sexual harassment case in the United States, Jenson vs. Eveleth Mines, where a woman who endured a range of abuse while working as a miner filed and won the landmark 1984 lawsuit.
Director: Niki Caro | Stars: Charlize Theron, Jeremy Renner, Frances McDormand, Thomas Curtis
Votes: 44,936 | Gross: $18.32M
Perhaps another chick flick , since it focuses on a historic harrassment case. But Charlize Theron always does a great job, so it's a decent film.
24. Made in Dagenham (2010)
R | 113 min | Comedy, Drama, History
A dramatization of the 1968 strike at the Ford Dagenham car plant, where female workers walked out in protest against sexual discrimination.
Director: Nigel Cole | Stars: Sally Hawkins, Bob Hoskins, Andrea Riseborough, Jaime Winstone
Votes: 16,073 | Gross: $1.09M
Yet another feminist equal rights film, this time set in England. This is the second film that I referred to earlier, which is about the Ford automotive corporation.
25. Wall Street (1987)
R | 126 min | Crime, Drama
An impatient young stockbroker is willing to do anything to get to the top, including trading on illegal inside information taken through a ruthless, greedy corporate raider who takes the youth under his wing.
Director: Oliver Stone | Stars: Charlie Sheen, Michael Douglas, Tamara Tunie, Franklin Cover
Votes: 165,196 | Gross: $43.85M
26. Waitress (2007)
PG-13 | 108 min | Comedy, Drama, Romance
Jenna is a pregnant, unhappily married waitress in the deep south. She meets a newcomer to her town and falls into an unlikely relationship as a last attempt at happiness.
Director: Adrienne Shelly | Stars: Keri Russell, Nathan Fillion, Jeremy Sisto, Cheryl Hines
Votes: 48,830 | Gross: $19.07M
This is a thoroughly enjoyable movie, but Andy Griffith winds up being the real scene-stealer in this funny film. Jeremy Sisto is also very good. Of course, the main star, Keri Russell (later of The Americans is great).
27. Waiting... (I) (2005)
R | 94 min | Comedy
Young employees at ShenaniganZ restaurant collectively stave off boredom and adulthood with their antics.
Director: Rob McKittrick | Stars: Ryan Reynolds, Anna Faris, John Francis Daley, Justin Long
Votes: 106,152 | Gross: $16.12M
An exagerrated yet hilarious look at working in a restaurant.
28. Working Girl (1988)
R | 113 min | Comedy, Drama, Romance
When a secretary's idea is stolen by her boss, she seizes an opportunity to steal it back by pretending she has her boss' job.
Director: Mike Nichols | Stars: Melanie Griffith, Harrison Ford, Sigourney Weaver, Alec Baldwin
Votes: 62,420 | Gross: $64.00M
Even though this movie got several Oscar nominations, it was really over-rated. Still, as Labor Day movies go, it's a decent way to spend the holiday.
29. Bridget Jones's Diary (2001)
R | 97 min | Comedy, Drama, Romance
Bridget Jones is determined to improve herself while she looks for love in a year in which she keeps a personal diary.
Director: Sharon Maguire | Stars: Renée Zellweger, Colin Firth, Hugh Grant, Gemma Jones
Votes: 263,634 | Gross: $71.54M
Another chick flick! This is actually a very good movie - the main reason it's so low on this list is because although the main character's work life is also a significant part of the plot, it takes a back seat to her love life. Remember, this is a list of Labor Day films, not romances!
30. Horrible Bosses 2 (2014)
R | 108 min | Comedy, Crime
Dale, Kurt and Nick decide to start their own business but things don't go as planned because of a slick investor, prompting the trio to pull off a harebrained and misguided kidnapping scheme.
Director: Sean Anders | Stars: Jason Bateman, Jason Sudeikis, Charlie Day, Jennifer Aniston
Votes: 184,840 | Gross: $54.45M
This film isn't nearly as funny as the first one, but isn't that almost always the case with sequels? It's still worth a look.
31. Short Time (1990)
PG-13 | 97 min | Action, Comedy, Crime
When a police detective thinks he is dying and learns that his life insurance pays out more if he dies in the line of duty, he tries to make that happen.
Director: Gregg Champion | Stars: Dabney Coleman, Matt Frewer, Teri Garr, Barry Corbin
Votes: 2,645 | Gross: $4.01M
A very amusing film, as long as you're not expecting an A-list, Academy Award winner. The main character is a cop about to retire from the force, when he gets bad news from his drug test that he's only got days to live. So he decides to get himself killed in the line of duty during his final months, so his family will be left with a better pension. He charges into danger and takes on criminals, but they all wind up surrendering (or missing him in shoot-outs), and he keeps earning praise as a hero, but he always survives. What he doesn't know is that his drug test was swapped in the lab with that of a bus driver, who begins cluelessly weaving all over the streets on his job. Can you tell yet that I like black humor?
32. Tapeheads (1988)
R | 93 min | Comedy, Music
A couple of creative losers accidently become big shots in the video music industry.
Director: Bill Fishman | Stars: John Cusack, Tim Robbins, Mary Crosby, Clu Gulager
Votes: 4,357 | Gross: $0.34M
John Cusack and Tim Robbins are remarkable in this very early film of theirs, as two music-video producers trying to break into the business.
33. Dinner for Schmucks (2010)
PG-13 | 114 min | Comedy
After he finds out that his work superiors host a dinner celebrating the idiocy of their special guests, a rising executive questions the merits of his invitation just as he befriends a man who would be the perfect guest.
Director: Jay Roach | Stars: Steve Carell, Paul Rudd, Stephanie Szostak, Zach Galifianakis
Votes: 111,117 | Gross: $73.03M
This film is silly and dorky to the point of eliciting groans as you watch it. Nevertheless, there are some very amusing moments. Steve Carell has done better (The Office; Little Miss Sunshine; The 40-Year Old Virgin) but he's also done worse (Evan Almighty).
34. Employee of the Month (2006)
PG-13 | 103 min | Comedy, Romance
A slacker competes with a repeat winner for the "Employee of the Month" title at work, in order to gain the affections of a new female employee.
Director: Greg Coolidge | Stars: Jessica Simpson, Dane Cook, Dax Shepard, Andy Dick
Votes: 50,153 | Gross: $28.44M
In spite of a decent supporting cast of character actors, this is NOT a great movie, but it has it's funny moments here and there.
35. Hijacking Hollywood (1997)
R | 91 min | Comedy
An aspiring director working as a lowly production assistant, conspires with his aspiring producer roommate to steal the reels of a mega budgeted film he's working on.
Director: Neil Mandt | Stars: Henry Thomas, Scott Thompson, Mark Metcalf, Neil Mandt
Votes: 295 | Gross: $0.00M
Not that great a film, but memorable simply because an abused and overworked low-rung-on-the-totem-pole finally gets a chance to exact a little revenge on his abusive bosses.
36.
Married... with Children (1987–1997)
Episode:
Hot off the Grill
(1989)
TV-PG | 23 min | Comedy
On Labor Day, the gender roles are reversed when Al becomes the loafing one while he forces Peggy to prepare the backyard barbecue for his creation of the famous "Bundy Burgers." But one of... See full summary »
Director: Gerry Cohen | Stars: Ed O'Neill, Katey Sagal, David Garrison, Amanda Bearse
Votes: 807
This one's a TV episode, but it takes place on Labor Day Weekend, so it seemed appropriate to include it here.
37. The Office (2005–2013)
TV-14 | 22 min | Comedy
A mockumentary on a group of typical office workers, where the workday consists of ego clashes, inappropriate behavior, and tedium.
Stars: Steve Carell, Jenna Fischer, John Krasinski, Rainn Wilson
Votes: 711,908
And here's a few TV series worth mentioning. The best of which is the American version of The Office.
38. The Office (2001–2003)
TV-MA | 30 min | Comedy, Drama
The story of an office that faces closure when the company decides to downsize its branches. A documentary film crew follow staff and the manager David Brent as they continue their daily lives.
Stars: Ricky Gervais, Martin Freeman, Mackenzie Crook, Lucy Davis
Votes: 123,178
Here's a few TV series worth mentioning. Second best is the original British version of The Office, created by comedian Ricky Gervais.
39. Outsourced (2010–2011)
TV-14 | 30 min | Comedy
A manager is sent to India to oversee a staff of customer service representatives.
Stars: Ben Rappaport, Anisha Nagarajan, Diedrich Bader, Parvesh Cheena
Votes: 12,746
Here's a few TV series worth mentioning. This came about a few years after the foreign film of the same name, which appeared higher up the list. It's a shame it didn't last longer - I love it!
40. Roadies (2016)
TV-MA | 60 min | Comedy, Drama, Music
A road crew helps with a rock band's major multi-city tour.
Stars: Carla Gugino, Luke Wilson, Imogen Poots, Rafe Spall
Votes: 6,119
Here's a few TV series worth mentioning. I'm not sure if this is going to be back next season, or if this was a one-off series, as it just wrapped up this summer of 2016. I certainly hope it continues, as it's my wife's and my favorite recent show. UPDATE: Sadly this series will NOT be returning. I recently heard a Ron White interview on the radio, where he said the series was not being renewed past it's first season, but he then he added that it was OK with him, since his character died off at the end of the first season anyway. LOL
41. Dirty Jobs (2005– )
TV-14 | 60 min | Reality-TV
Follows the exploits of Mike Rowe as he performs various dirty and dangerous jobs around the USA.
Stars: Mike Rowe, David M. Barsky, Doug Glover, Troy Paff
Votes: 9,506
Here's a few TV series worth mentioning.
42. Dirty Jobs (2007)
30 min | Documentary, Action, Reality-TV
Hosts Ben Dark and Jo Beth Taylor assume the roles of some the more hands on, obscure jobs which may not be for everyone, but are essential to everyday life.
Stars: Ben Dark, Peter Schmeichel, Jo Beth Taylor
Votes: 1,146
Here's a few TV series worth mentioning.
43. Working (1997–1999)
30 min | Comedy
What do you do after graduating from university? Go to work. And that's exactly what Matt wants to do. He wants to climb the corporate ladder the old-fashioned way: by working.
Stars: Fred Savage, Maurice Godin, Yvette Freeman, Arden Myrin
Votes: 556
Here's a few TV series worth mentioning.
44. Herman's Head (1991–1994)
30 min | Comedy
The four aspects of a man's personality help him get through different situations in life.
Stars: William Ragsdale, Hank Azaria, Jane Sibbett, Yeardley Smith
Votes: 2,564
Here's a few TV series worth mentioning.
45. Falling Down (1993)
R | 113 min | Action, Crime, Drama
An ordinary man frustrated with the various flaws he sees in society begins to psychotically and violently lash out against them.
Director: Joel Schumacher | Stars: Michael Douglas, Robert Duvall, Barbara Hershey, Rachel Ticotin
Votes: 206,710 | Gross: $40.90M
46. Taxi Driver (1976)
R | 114 min | Crime, Drama
A mentally unstable veteran works as a nighttime taxi driver in New York City, where the perceived decadence and sleaze fuels his urge for violent action.
Director: Martin Scorsese | Stars: Robert De Niro, Jodie Foster, Cybill Shepherd, Albert Brooks
Votes: 920,909 | Gross: $28.26M
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