An incredibly recognizable face for years to anyone who watches both TV series and movies, has always had memorable roles. He rarely fades into the background of his projects, often delivering standout line readings or doing something unexpected. Throughout his career, he has done an excellent job of balancing both dramatic and comedic roles, showcasing his versatility and keeping himself consistently working for over 40 years. Cole took over for Mark Harmon as the lead on NCIS, joining the show in 2021.

Cole has a unique presence on screen and often provides moments that audiences talk about long after the credits roll. He’s a dependable performer who typically finds himself at the center of something memorable. While some may prefer his dramatic roles, many fans know and love him for his comedic performances. Some of these roles are more iconic than others.

Here is a list of Gary Cole’s best comedic roles, ranked from those fans should definitely know to the ones they almost certainly already love.

Using an iconic television series as the basis for a movie is not a completely wild idea. The A-Team had a successful film reboot in the 2000s. Back in 1995, Gary Cole was cast as Mike Brady in The Brady Bunch Movie, a film that continued the storylines of the classic series—but with a modern twist. The quirk of the film is that it takes place in the present day, yet the Bradys still act like it’s the 1970s. Cole delivers a memorable performance as the ever-earnest patriarch, whose failure to pay property taxes threatens the repossession of their iconic house.

Shelley Long starred alongside Cole as Carol Brady, and the film featured cameos from several original Brady Bunch cast members, including Florence Henderson as Carol’s mother. Christine Taylor also gave a standout performance as Marcia Brady. The movie is pure, silly fun, and it even spawned two sequels: A Very Brady Sequel and The Brady Bunch in the White House—all three starring Cole and Long. Luckily for everyone, there was no Cousin Oliver in this remake.

In the sports satire Dodgeball: A True Underdog Story, Gary Cole teams up with Jason Bateman’s Pepper Brooks as the eccentric dodgeball commentating duo on ESPN’s fictional “The Ocho” channel. Cole plays Cotton McKnight, the straight-laced play-by-play announcer, and he and Bateman thrive with the hilarious lines they’re given. The film stars Vince Vaughn as the owner of a failing gym being targeted for acquisition by a corporate fitness chain run by Ben Stiller’s over-the-top character. To raise the money needed to save his gym, Vaughn’s character enters a high-stakes dodgeball tournament in hopes of winning the grand prize.

Stiller’s character assembles a rival team, setting the stage for a chaotic and comedic showdown. Cole once again shares the screen with Christine Taylor, who plays one of the key members of Vaughn’s team. McKnight’s calls include gems like “Do you believe in unlikelihoods?”—a parody of Al Michaels’ legendary “Do you believe in miracles?” line from the Miracle on Ice. Cole and Bateman clearly have a blast in their roles, leading the audience through the absurd action with infectious energy.

If a sequel ever materializes, fans will surely hope the iconic announcing duo makes a triumphant return.

Cole's Andrew Klein was a character introduced in Season 5 of Entourage. He is a former coworker of Jeremy Piven's Ari Gold and is hired by Ari to his new firm. Season 6 features a massive arc with Klein, who has an extramarital affair with a young agent, causing a ton of problems for Ari. The quick-wittedness of the scripts keeps the insults flying out of Ari's mouth towards his friend (and pretty much everyone else) as he tries to figure out a solution to helping out Andrew.

The episodes where Ari has to intervene in Andrew's life, which is spiraling after his wife finds out about the affair, bring the classic comedic tension that Entourage and Piven were known for during their run. Klein ultimately makes it all up to his boss by bringing Aaron Sorkin in as a client. Maybe he'll return the favor and write for the proposed Entourage reboot.

It can be hard to shine in a movie starring the tour de force that is Melissa McCarthy, but Cole does have a few standout scenes in 2014's Tammy. The film stars McCarthy as the titular character, a rude and boisterous woman who goes on a road trip to Niagara Falls with her grandma, Pearl, played by Susan Sarandon. Cole's character, Earl, meets the pair in a bar in Louisville, Kentucky, where he takes a liking to Pearl. An incredibly flirty scene takes place, with Earl using incredibly cheesy pick-up lines and glances, all of them working on Pearl.

Tammy strikes up a conversation and relationship with Earl's son, Bobby, played by Mark Duplass. Both couples spend the night drinking and hooking up, which is probably more than audiences needed to see from Sarandon and Cole. The film made over $100 million at the box office, thanks to McCarthy's reputation and comedic timing. Maybe Earl's advances and charm also brought women into the theater.

Blockers was a teen comedy featuring Leslie Mann, Ike Barinholtz, and John Cena as parents trying to stop their daughters from losing their virginities on prom night. The film has three strong performances from the lead stars, all portraying concerned parents who are meddling in their children's business for what they believe is good reason. The movie is as much about showing up for your kids as it is about stopping teens from having sex.

Cole plays Ron, the father of one of the boys who is dating one of the girls. The prom after-party is slated to be at Ron and his wife's house. The three girls' parents head to Ron's house to try and talk to him before the party, and they walk in on him and his wife, Gina Gershon, playing a sex game. Hilarity ensues, with mistaken identities and dirty talk. Cole's line delivery during this scene makes it one of his better comedy performances.

Cole has been providing the voice of Principal Shepherd, the principal at James Wood High School where Meg and Chris Griffin go to school, in Family Guy since 2000. Cole has voiced other characters over the past 25 years as well, but he has voiced Shepherd in over 90 episodes since the beginning of the show. Principal Shepherd often comes out of nowhere with one snide remark or offhand comment, punctuating a joke.

Cole's dry and even-keeled delivery for the character adds to his legend. From episodes where he only has a line or two to ones where he is the focus, Shepherd always delivers a ridiculous moment that highlights just how absurd the show can be. One standout episode sees him moving in with the Griffins after losing his job—a scenario that’s arguably the highlight of the character's appearances.

Ted Jones is a ruthless drug lord in Pineapple Express, the stoner comedy starring James Franco and Seth Rogen. Rogen's character, Dale, happens to be in the wrong place at the wrong time and witnesses Jones kill a rival gangster. This sets off a wild chase as Jones and his henchmen search for Dale and his drug dealer, Saul, played by Franco, throughout the film. Cole brings a suaveness to Jones that seems irresistible.

There’s a big twist involving Jones that makes his character even more conniving. He has the innate ability to identify the strain of marijuana just by smelling it, which leads to his pursuit of Saul and Dale. A massive shootout in Ted’s lair becomes one of the most memorable parts of the film. Jones is a sleazy guy, and Cole plays him just right in one of the better studio comedies of the 2000s.

Reese Bobby is a deadbeat dad and a drunk who unknowingly shaped his son's entire life with one sentence he said when the boy was very young. Cole's character in Talladega Nights: The Ballad of Ricky Bobby is not someone who should be celebrated, as he abandoned his family only to show up again years later. But the line “If you’re not first, you’re last” became the most impactful thing he ever said to his son—and it made Ricky who he is.

That worked fine while Ricky was a successful NASCAR driver, but when he loses his ability to drive, Reese comes back into his life and teaches him how to be Ricky again. Cole kills this role in the Adam McKay–directed film as the loser dad who uses unorthodox methods to help Ricky overcome his fear of driving. The two most memorable scenes are when he puts a live cougar in the car and makes Ricky drive it, and when he makes Ricky drive blindfolded.

Cole starred as Kent Davison, a senior strategist to the President in Veep, the HBO comedy starring Julia Louis-Dreyfus as the Vice President of the United States who eventually becomes President. Kent is a main character in Seasons 4–7 but appeared sparingly in Seasons 2 and 3. He is robotic in nature, which infuriates Kevin Dunn’s Ben to no end. However, he’s great with numbers and understands polling better than almost anyone else in the White House, making him indispensable during Selina Meyer’s campaigns.

Cole’s dry line deliveries are hysterical—especially because he rarely gets the jokes thrown at him. They tend to go over his head, and he responds in a cold and calculated way, which makes the humor land even harder. Cole starred in 55 episodes of the show and was nominated for a Primetime Emmy Award for his role.

This is the comedy role Cole will be most known for for the rest of his life. It’s unequivocal, as Office Space has been a popular movie that has been revisited by many since it premiered in 1999. He stars as Bill Lumbergh, the boss of Ron Livingston's Peter. Lumbergh has a smarmy way about him and always seems to be pestering Peter about something work-related. The reason why Lumbergh is such a memorable character is that plenty of audiences know someone like him or have dealt with a superior at work who resembles him.

Cole’s performance is exacting and perfect because Lumbergh wields his power with a sense of entitlement, and his voice and cadence alone would be enough to drive any employee insane. The entire world knows what TPS reports are because of Bill Lumbergh. Cole’s iconic "villain" is one of the most recognizable of the 1990s and stands the test of time because of how annoying he is.