Gary Cole: 10 Best Movies & TV Shows

As one of the great character actors working today, Gary Cole’s movies and TV roles feature many fan-favorite and acclaimed performances across an incredible array of projects. Cole is the kind of actor whom fans instantly recognize from any number of roles. As a sign of his versatility, he might be best known for a chilling villain performance just as often as he is recognized for a hilarious comedic turn. However, there are several movies and TV shows from his career that stand out as the best and the best display of his talent.

Cole has held his own against some truly great comedic actors over the years, such as Ben Stiller, Julia Louise-Dreyfus, and Will Ferrell. However, he has also been menacing or sternly serious in movies both on the small screen and on the big screen. He has made his mark on a number of hit series and even led a few projects himself. With such an impressive career, Gary Cole’s best movies and TV shows are truly exceptional.

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10 The Brady Bunch Movie (1995)

As Mike Brady

Gary Cole is one of the best comedic actors when it comes to playing ridiculous roles with hilarious sincerity. That is perfectly on display in one of his most underrated movies, The Brady Bunch Movie. Based on the beloved sitcom of the past, the movie takes a look at the unconventional family that is established when single father Mike Brady (Cole) marries single mother Carol (Shelley Long), with a combined blended family, making for a hectic household.

What makes The Brady Bunch Movie such a clever television adaptation is that it completely embraces the fact that the show, its tone, and its style were outdated in the 1990s. The show takes place in the ’90s, but the Brady family looks like they stepped out of the ’70s with their fashion and demeanor making them a family of oddballs. Cole is especially hilarious at delivering the cliché father-knows-best role with a straight face, as the movie points out how silly it seems now.

9 Entourage (2004-2011)

As Andrew Klein (12 Episode, 2008-2010)

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Vincent Chase, a young and talented actor, embarks on his Hollywood journey surrounded by his loyal friends from Queens. His inner circle includes Eric, his dedicated manager; Johnny Drama, his supportive but fame-seeking half-brother; Turtle, his fun-loving and resourceful friend; and Ari Gold, his fiercely determined agent. Together, they navigate the complexities of the entertainment industry, balancing career aspirations with personal relationships, and facing the ups and downs of fame with camaraderie and resilience.

Cast Kevin Connolly , Adrian Grenier , Kevin Dillon , Jerry Ferrara , Jeremy Piven , Debi Mazar , Perrey Reeves , Rex Lee , Rhys Coiro , Gary Cole , Emmanuelle Chriqui , Scott Caan Release Date July 18, 2004 Seasons 8 Creator(s) Doug Ellin

Throughout his career, Gary Cole has shown an ability to join the cast of an ongoing series and immediately fit into the fold of the story. Such was the case with Entourage, which was already a hit comedy series on HBO by the time Cole joined in the fifth season. The series is loosely based on the Hollywood experiences of Mark Wahlberg, and follows up-and-coming movie star Vincent Chase (Adrian Grenier) as he embraces the life of luxury while bringing his childhood friends along for the ride.

Cole joins the show as Andrew Klein, a former friend of Ari Gold (Jeremy Piven) who joins his agency. What began as a simple guest-starring role blossomed into his being a series regular on the series. Cole mixes intensity and comedy with Andrew’s wild storylines, which include an affair with a fellow agent and his battle with addiction. However, despite the serious subject matter the show always maintained its sense of fun and wish-fulfillment throughout.

8 American Gothic (1995-1996)

As Sheriff Lucas Buck

american gothic Not RatedMystery Cast Dylan Bruce , Elliot Knight , Maureen Sebastian , Antony Starr , Megan Ketch , Gabriel Bateman , Stephanie Leonidas , Justin Chatwin , Virginia Madsen , Jamey Sheridan , Juliet Rylance

Gary Cole’s first starring role on television is also one of his most overlooked projects. American Gothic is a dark supernatural thriller that stars Cole as Sheriff Lucas Black, a seemingly friendly and helpful small-town sheriff who is really a sadistic murderer backed by evil forces. The series focuses on a young boy with a dark connection to Black who, along with his allies, seeks to bring the sheriff down.

The series was perhaps ahead of its time with the dark and twisted storylines kicking off right from the first episode. The show only lasted one season before it was canceled, despite positive reviews from critics, especially about Cole’s performance. However, in the years since it ended, American Gothic has gained a cult following as well as a reputation as a show that ended too soon.

7 Dodgeball: A True Underdog Story (2004)

As Cotton McKnight

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Dodgeball: A True Underdog Story is a 2004 comedy directed by Rawson Marshall Thurber and starring Vince Vaughn. Vaughn plays Peter La Fleur, the owner of a struggling gym who has fallen behind on payments. But after White Goodman (Ben Stiller) threatens to buy his competitor’s gym, Peter and his gang enter a dodgeball tournament to raise money.

Director Rawson Marshall Thurber Release Date June 18, 2004 Cast Vince Vaughn , Christine Taylor , Ben Stiller , Rip Torn , Justin Long , Stephen Root Runtime 92 minutes

The sports comedy Dodgeball: A True Underdog Story is one of many examples of Gary Cole managing to stand out in a comedy with a stacked ensemble of funny people. Dodgeball stars Vince Vaughn as the easy-going owner of a gym for average people who is being run out of business by an aggressive fitness guru (Ben Stiller). In order to get the money to save the gym, Vaughn and his loyal customers form a team to enter a dodgeball tournament in the hopes of winning the cash prize.

While Vaughn and Stiller are hilarious and the dodgeball sequences are great moments of slapstick comedy, the highlight of the movie is the tournament comedy provided by Gary Cole and Jason Bateman as two mismatched announcers. While Batman’s Pepper Brooks is a dim-witted and unpredictable color commentator, Cole is just as funny in playing his character of Cotton McKnight as if this is a pivotal moment in sports. While there are always talks of Dodgeball 2 happening, it would not be the same if Cole and Bateman didn’t return.

6 Pineapple Express (2008)

As Ted Jones

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Seth Rogen helped craft the story and screenplay for this 2008 Comedy and Action film, along with Judd Apatow. Starring Rogen and James Franco, the story follows a pair of marijuana enthusiasts that witness a murder by corrupt police officers and are forced to run for their lives.

Director David Gordon Green Release Date August 6, 2008 Cast Kevin Corrigan , Seth Rogen , Danny McBride , James Franco , Craig Robinson , Gary Cole Runtime 111 minutes

Gary Cole had the rare opportunity to showcase his intimidating side as a villain while also playing around in a goofy comedy. Pineapple Express comes from the mind of Seth Rogen and serves as a mix of an action movie throwback and a stoner comedy. Rogen plays a process server who accidentally witnesses a mob hit involving corrupt police officers. He then goes on the run with his dim-witted but kind-hearted drug dealer (James Franco).

Cole plays Ted Jones, the drug lord who goes in search of the two half-baked heroes. Cole adds an appropriate menace to the movie, as the action sequences in Pineapple Express are legitimately impressive. However, the movie is also laugh-out-loud funny, with Rogen and Franco showing off their hilarious chemistry and Danny McBride delivering a breakout performance as the drug dealer Red, who cannot seem to die.

5 Talladega Nights: The Ballad Of Ricky Bobby (2006)

As Reese Bobby

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Talladega Nights: The Ballad of Ricky Bobby is a 2006 comedy directed by Adam McKay, starring Will Ferrell and John C. Reilly. Ferrell plays a successful NASCAR driver who almost loses his family, best friend, and his career when a French Formula One driver attempts to take his number one spot in the world of racing.

Director Adam McKay Release Date August 4, 2006 Cast Will Ferrell , John C. Reilly , Sacha Baron Cohen , Gary Cole , Michael Clarke Duncan , Leslie Bibb , Jane Lynch , Amy Adams Runtime 108 Minutes

Gary Cole is able to steal laughs from even the funniest actors in Hollywood, as evidenced by the hilarious sports comedy Talladega Nights: The Ballad of Ricky Bobby. Will Ferrell stars as Ricky Bobby, a NASCAR driver whose quick rise to fame in the sport has led to him becoming a massive success while also adding to his ever-growing ego. However, it is all put in jeopardy with the arrival of a Formula One driver (Sacha Baron Cohen) who seeks to end Ricky’s reign at the top.

Cole is hilarious as Reese Bobby, Ricky’s reckless outlaw father who pops in and out of his life while also inadvertently inspiring him to be a racer in the first place. Cole is certainly having a lot of fun as the wild character and he fits perfectly into the hilarious hijinks of the movie. Ferrell also delivers another terrific comedic performance and has particularly great chemistry with John C. Reilly in their first collaboration together.

4 The West Wing (1999-2006)

As Vice President Bob Russell (22 Episodes, 2003-2006)

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In Aaron Sorkin’s classic political procedural, the senior staff of President Josiah Bartlet (Martin Sheen) face the daily challenge of helping to run the country from the West Wing of the White House. The series features an ensemble cast that also includes Rob Lowe, Dulé Hill, Bradley Whitford, Allison Janney, Richard Schiff, and John Spencer. 

Cast Martin Sheen , Bradley Whitford , Allison Janney Release Date September 22, 1999 Seasons 7

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The West Wing is another excellent series that Gary Cole effortlessly stepped into while it was already underway. Created by Aaron Sorkin, The West Wing is a behind-the-scenes look at the White House staff under President Jed Bartlet (Martin Sheen). Together they deal with international crises, assassination attempts, and re-election campaigns while also doing their best to better America in their own way.

Cole joined the series in season 5 as Bob Russell, who becomes the second Vice President of the United States under Bartlet, and the actor does a great job of playing the complicated character. Russell is not the most effective or skilled politician, but there is a charm in him knowing that and using his particular strengths to bolster his career. The series is a wonderfully written drama that offers an exciting look at the political world, even if it is an idyllic one.

3 A Simple Plan (1998)

As Vernon Bokovsky / FBI Agent Neil Baxter

A Simple Plan RCrimeDramaThriller

A Simple Plan centers on three men who discover a crashed plane filled with over four million dollars in cash. Directed by Sam Raimi, the film stars Bill Paxton, Billy Bob Thornton, and Bridget Fonda. Their decision to keep the money leads to unforeseen consequences and moral dilemmas, ultimately unraveling their lives. Based on the novel by Scott B. Smith, the film explores themes of greed, deception, and the human condition.

Director Sam Raimi Release Date December 11, 1998 Cast Bill Paxton , Billy Bob Thornton , Bridget Fonda , Brent Briscoe , Jack Walsh , Chelcie Ross , Becky Ann Baker , Gary Cole Runtime 121 Minutes

After delivering the iconic Evil Dead movies and before he kicked off the Spider-Man trilogy, Sam Raimi delivered one of his best and most underrated movies with the crime story A Simple Plan. The movie stars Bill Paxton and Billy Bob Thornton as two brothers who happen upon a plane that crashed in the forest with a bag of money inside. Presented with this new wealth, the brothers concoct a plan to keep the money secret, only for it to spiral out of control with deadly consequences.

Cole only appears in the climax, playing Vernon Bokovsky, the man who comes to the small snowy town looking for his lost money. Instantly, Cole adds a sense of menace to the final moments of the movie, delivering a memorable villain performance with the limited screen time that he has. Raimi crafts a brilliant dark crime story with an underlying sense of humor that makes it feel like a Coen brothers movie.

2 Veep (2012-2019)

As Kent Davison (55 Episodes, 2013-2019)

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When former U.S. Senator Selina Meyer becomes Vice President of the United States, she finds that it is less like what she hoped for, and more what people warned her it would be.

Cast Anna Chlumsky , Timothy Simons , Julia Louis-Dreyfus , Reid Scott , Tony Hale , Matt Walsh , Kevin Dunn , Sufe Bradshaw Release Date April 22, 2012 Seasons 7 Showrunner Armando Iannucci

While Gary Cole is the kind of actor who can pop up in numerous TV shows of any genre, his best series was the hilarious political satire Veep. As if her iconic turn on Seinfeld was not enough, Julia Louise-Dreyfus delivers another legendary television performance as Selina Meyer, who starts the show as the ignored and overlooked Vice President of the United States of America. She then uses every dirty trick and shady deal she can think of to grab onto any ounce of power she can.

Along with Louise-Dreyfus’ amazing performance in the lead role, the cast of Veep is outstanding, with a colorful ensemble of characters showing off the hilarious dark side of politics. Cole joined the show in the second season as strategist Kent Davison, fitting perfectly into the cast. Cole is hilarious in playing the character who is described as cold and robotic yet has so many laugh-out-loud moments.

1 Office Space (1999)

As Bill Lumbergh

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Office Space is a satirical comedy movie by Mike Judge, the creator of Beavis and Butthead and King of the Hill. Peter Gibbons, the film’s protagonist, is overworked, underpaid, and over it all as his work continues to wreak havoc on his personal life and mental health. One day during a hypnosis session, Peter’s therapist dies mid hypnosis leaving Peter in a perpetual state of calm, where he is no longer bothered by the trivial elements of the world. With a changed outlook and a devil-may-care attitude, Peter’s newfound love of life starkly contrasts with the rest of the world and the hustle approach evident in American work culture. 

Director Mike Judge Release Date February 19, 1999 Cast Stephen Root , Ron Livingston , Gary Cole , John C. McGinley , Jennifer Aniston Runtime 89 minutes

Office Space is one of those comedies that was a box office bomb when it was initially released but has since grown into a cult classic and is now viewed as one of the funniest movies of the 1990s. From King of the Hill creator Mike Judge, Office Space stars Ron Livingston as a man working at a soul-crushing corporate job with mundane tasks and micro-managing bosses who decides to take a new approach by simply not caring about his job anymore.

Office Space is filled with hilarious quotes and colorful characters, so it is all the more impressive that Gary Cole steals the entire show as Bill Lumbergh, the intrusive and painfully dull office supervisor. Cole gives a perfect comedic performance, creating this totally unique yet wholly recognizable character. From the way he sips his coffee to his constant use of “Yeaaaaaaaaa ah…”, it is Cole’s best performance and a comedy gem.

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