Gary Cole’s Top 10 Hilarious Roles That Will Shock You

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For decades, Gary Cole has been a highly distinguishable figure to audiences who enjoy both television shows and films. Known for his unforgettable performances, he seldom blends into the backdrop of his productions. Instead, he often steals the spotlight with captivating line deliveries or surprising actions. Throughout his illustrious career, Cole has demonstrated an impressive ability to balance dramatic and comedic roles, displaying his versatility and ensuring steady employment for over four decades. Starting in 2021, Cole assumed the lead role from Mark Harmon on NCIS.

Cole consistently leaves an indelible impression on screen, generating discussions among viewers even after the movie ends. He’s a reliable actor who often takes center stage in unforgettable scenes or events. While some fans admire his dramatic work, many more cherish him for his comedic performances. Some of these roles have become iconic, standing out more than others.

Here’s a compilation of Gary Cole’s top comedic performances, arranged from must-see roles to those you likely adore deeply.

10
Mike Brady

‘The Brady Bunch Movie’ (1995)

Utilizing a popular TV show as the foundation for a film adaptation isn’t always an outlandish concept. For instance, “The A-Team” was successfully revived on the big screen in the 2000s. In 1995, Gary Cole portrayed Mike Brady in “The Brady Bunch Movie,” a film that extended the story arcs from the classic series while infusing it with a contemporary flavor. The unique aspect of this film is its setting: despite being set in the present day, the Bradys behave as if they’re still living in the 1970s. Cole offers an endearing portrayal of the dedicated father figure, whose oversight on property taxes places their iconic home at risk of repossession.

Shelley Long appeared alongside Cole as Carol Brady, and the movie included appearances from several original “Brady Bunch” cast members, such as Florence Henderson portraying Carol’s mother. Christine Taylor delivered an impressive performance as Marcia Brady. This film offers nothing but enjoyable, goofy entertainment, and it led to two follow-ups: “A Very Brady Sequel” and “The Brady Bunch in the White House,” with both Cole and Long starring in all three. Fortunately for everyone, this reboot did not include a Cousin Oliver character.

9
Cotton McKnight

‘Dodgeball: A True Underdog Story’ (2004)

In the comedic sports film titled “Dodgeball: A True Underdog Story,” Gary Cole and Jason Bateman form an unusual commentary team on the fictitious ESPN channel, “The Ocho.” Cole portrays Cotton McKnight, a strict play-by-play announcer, while Bateman brings life to the humorous dialogue they’re provided. The story follows Vince Vaughn, who plays the owner of a struggling gym at risk of being bought by a corporate fitness chain run by Ben Stiller’s exuberant character. To save his gym, Vaughn’s character decides to participate in a high-risk dodgeball tournament with the goal of winning the substantial prize money.

In my perspective, I join forces with Stiller’s character to create an opposing squad, paving the way for a hilariously chaotic confrontation. Once again, I find myself alongside Christine Taylor, portraying a vital member of Vaughn’s crew. McKnight’s dialogue features witty remarks such as “Do you believe in unlikelihoods?”, a clever jab at Al Michaels’ iconic “Do you believe in miracles?” from Miracle on Ice. Together with Bateman, we relish our roles, guiding the viewers through the preposterous action with undeniable enthusiasm.

Should a sequel come about, fans can certainly anticipate that the renowned announcing team might gracefully reappear, making a victorious comeback.

8
Andrew Klein

‘Entourage’ (2004 – 2011)

In Season 5 of Entourage, a new character named Andrew Klein, previously associated with Jeremy Piven’s Ari Gold, was introduced. Ari subsequently hires him to his new company in Season 6. The storyline for this season revolves around an extramarital affair undertaken by Klein, which creates numerous complications for Ari. Throughout the series, Ari’s sharp-tongued dialogue delivers a barrage of insults towards Klein (and almost everyone else) as he attempts to resolve the predicament involving Andrew.

In episodes where Ari steps in to help Andrew, whose life is in turmoil following his wife discovering his affair, there’s a familiar comedic tension reminiscent of the duo’s work during their time on Entourage. Eventually, Klein manages to make amends with his superior by securing Aaron Sorkin as a client. Perhaps Sorkin will reciprocate by penning the script for the proposed revival of Entourage someday.

7
Earl Tillman

‘Tammy’ (2014)

In the 2014 film “Tammy,” it’s no small feat to outshine Melissa McCarthy’s captivating performance, but Cole manages to steal a few scenes. In this movie, McCarthy portrays Tammy, an assertive and spirited woman who embarks on a road trip with her grandmother, Pearl, played by the legendary Susan Sarandon. My character, Earl, encounters them in a bar in Louisville, Kentucky, where I find myself drawn to Pearl. A delightfully flirtatious exchange ensues, with me employing some rather cheesy pick-up lines and glances, each of which seems to resonate with Pearl.

In a scene worth noting, Tammy initiates a chat and bond with Bobby, who is portrayed by Mark Duplass as Earl’s son. The night unfolds with both pairs sharing drinks and developing intimacy, an event that might have been excessive for some viewers given the on-screen presence of Sarandon and Cole. However, this film managed to rake in over $100 million at the box office, largely due to McCarthy’s star power and her knack for humor. It’s also possible that Earl’s charisma might have attracted more female moviegoers to the theater.

6
Ron

‘Blockers’ (2018)

As a devoted parent, I found myself immersed in “Blockers,” a hilarious teen comedy starring Leslie Mann, Ike Barinholtz, and John Cena, who all brilliantly portrayed the roles of overprotective parents. Their characters were determined to prevent their daughters from losing their virginity on prom night, driven by what they perceived as good intentions. However, this movie isn’t just about stopping teenagers from becoming sexually active; it’s also a heartwarming tale about the importance of being there for your kids and supporting them through life’s milestones.

In a twist of events at the upcoming prom after-party, it turns out that the venue is Ron, the father of one of the young ladies’ date, and his wife’s house. Before the festivities kick off, the three girls’ parents pay a visit to Ron’s residence with the intention of speaking with him prior to the party. However, they unexpectedly stumble upon an intimate moment between Ron and his wife, Gina Gershon, engaged in a rather explicit game. The ensuing chaos is filled with comedic misunderstandings and raunchy dialogues. Cole’s delivery during this scene is particularly noteworthy, showcasing one of his finest comic performances.

5
Principal Shepherd

‘Family Guy’ (1999 – Present)

Cole has been lending his voice to the character of Principal Shepherd, the principal at James Wood High School where Meg and Chris Griffin attend school in the TV show Family Guy, since 2000. Over the past 25 years, Cole has provided voices for various characters, but he has voiced Principal Shepherd in more than 90 episodes of the series. Throughout the show, Principal Shepherd frequently makes unexpected appearances with a witty remark or casual comment, serving as a punchline to many jokes.

Cole’s calm and composed acting style enhances his legendary portrayal. Whether he has just a few lines or takes center stage, Shepherd consistently provides a hilarious moment, showcasing how outrageous the series can get. One particular episode that stands out is when his character moves in with the Griffins following job loss – an event that could be considered the peak of his on-screen appearances.

4
Ted Jones

‘Pineapple Express’ (2008)

In the stoner comedy “Pineapple Express,” I found Ted Jones to be an unyielding kingpin of the drug trade. It’s James Franco and Seth Rogen who star in this film, with Rogen’s character, Dale, finding himself in a precarious predicament – accidentally witnessing Jones brutally eliminate a rival gangster. This incident ignites a thrilling chase as Jones and his cronies relentlessly pursue Dale and his dealer, Saul (played by Franco), across the movie. Cole delivers a captivating coolness to Jones that leaves one spellbound.

In a surprising turn of events, Jones’ character becomes even more cunning due to a plot twist. His unique talent lies in his uncanny ability to distinguish different strains of marijuana merely by its smell, driving his relentless chase after Saul and Dale. One unforgettable scene is the intense gunfight that unfolds in Ted’s hideout, adding to the film’s overall impact. Jones is portrayed as a slippery character, and Cole delivers an impressive performance as he brings Jones to life in one of the standout studio comedies from the 2000s.

3
Reese Bobby

‘Talladega Nights: The Ballad of Ricky Bobby’ (2006)

As a passionate movie-goer, I’d say: In the film “Talladega Nights: The Ballad of Ricky Bobby,” Reese Bobby, my character’s flawed father, was a chronic underachiever and heavy drinker. He wasn’t someone to be idolized, as he deserted his family for years, but then reappeared. Yet, the phrase “If you’re not first, you’re last” that he casually dropped when my son was very young had an immense impact on him and shaped who Ricky Bobby ultimately became. That single sentence resonated deeply and defined Ricky’s life trajectory.

In the thrilling world of NASCAR, I thrived as Ricky, raking in wins left and right. But when fate stripped me of my driving privileges, life took a turn for the unexpected. Reese, an old acquaintance from my past, re-entered my world, guiding me on a journey to rediscover myself.

In the masterful direction of Adam McKay, Cole delivers an unforgettable performance as the eccentric father figure who employs unusual tactics to help Ricky conquer his dread of being behind the wheel. The movie is filled with two scenes that leave audiences gasping in awe – when he places a live cougar in the car and forces me to drive, and when I have to navigate the track blindfolded. These instances showcase the lengths Cole’s character goes to help Ricky face his fears and find his way back to the driver’s seat.

2
Kent Davison

‘Veep’ (2012 – 2019)

Cole played the role of Kent Davison, a top strategist to the President in the HBO comedy series “Veep,” where Julia Louis-Dreyfus portrayed the Vice President who eventually became President. Kent is a significant character from Seasons 4 through 7, although he appeared less frequently in Seasons 2 and 3. He’s characterized by being mechanical, which consistently annoys Kevin Dunn’s character, Ben. However, Kent excels at numbers and has a deep understanding of polling, making him essential during Selina Meyer’s election campaigns.

Cole’s deadpan delivery is hilarious, particularly since he seldom catches the jests aimed at him. More often than not, they fly over his head, prompting him to react coolly and precisely, which amplifies the humor. Cole featured in 55 episodes of the series and earned a Primetime Emmy Award nomination for his portrayal.

1
Bill Lumbergh

‘Office Space’ (1999)

For the remainder of his career, Cole will likely be recognized most prominently for his comedic role in “Office Space,” a film that has endured popularity since its debut in 1999 and continues to be rewatched by many. In this movie, he plays Bill Lumbergh, the boss of Ron Livingston’s character Peter. Lumbergh is characterized by his oily demeanor and persistent queries about work-related matters that often annoy Peter. The reason Lumbergh remains such a vivid character is because audiences can relate to him, having encountered someone similar in their own workplaces or knowing someone who resembles him.

Cole’s acting is impeccable and spot-on, as Lumbergh exerts his authority with an air of arrogance, making even his tone and pace enough to drive any worker to the brink. The global recognition of TPS reports can be attributed to Bill Lumbergh. Cole’s iconic portrayal of the “villain” is one of the most memorable from the 1990s and continues to resonate due to his irritating nature.

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2025-05-19 04:34