Captain James T. Kirk is a heroic ideal in Star Trek: The Original Series, but when William Shatner turns on the charm and unveils his comedy chops, Captain Kirk is very funny. Shatner originated Captain Kirk in 1960s Star Trek, voiced Kirk in Star Trek: The Animated Series, and reprised Kirk in seven Star Trek movies.
In truth, Star Trek has always had humorous moments and has delved into pure comedy on several occasions throughout the many Star Trek TV series and movies. Star Trek: The Original Series' holy trinity of Captain Kirk, Mr. Spock (Leonard Nimoy), and Dr. Leonard McCoy (DeForest Kelly) is built upon their humorous banter.
Some moments when William Shatner was playing Captain Kirk straight still came off as intentionally humorous, such as Kirk's battle with the Gorn in Star Trek: The Original Series season 1's "Arena." Shatner's tussle with a man in a restrictive rubber costume endures as a campy example of classic Star Trek's limitations.
However, there are a handful of occasions when William Shatner went gung ho into playing Captain Kirk as funny in Star Trek (and outside of Star Trek), and the results are memorably hilarious. Here are the five best times when William Shatner left audiences in stitches as Captain Kirk.
5 Star Trek: The Original Series – “The Enterprise Incident”

At first watch, we take Star Trek: The Original Series season 3, episode 2, "The Enterprise Incident," at face value: Captain Kirk seems to have snapped, and illegally orders the Starship Enterprise into Romulan space in a treaty violation. Kirk behaves like a madman, and even Spock throws him under the bus.
When Captain Kirk is surgically altered into a Romulan, complete with sharp eyebrows and pointy ears, "The Enterprise Incident" emerges as a comedic tour de force by William Shatner, who was the only one besides Spock in on the joke the entire time.
4 Star Trek Generations

Star Trek Generations was predicated on the death of Captain Kirk as the monumental conclusion of the film's historic meeting between Kirk and Captain Jean-Luc Picard (Patrick Stewart). Before Kirk got whacked, however, William Shatner's charm and humor stole Star Trek Generations.
There are witty moments in Star Trek Generations' prologue as Captain Kirk passes the torch to Captain John Harriman (Alan Ruck) and the USS Enterprise-B. However, once Captain Picard finds Kirk in the Nexus, William Shatner goes on a full-on charm offensive when he meets the current Captain of the Enterprise.
3 Futurama – "Where No Fan Has Gone Before"

8 years after Star Trek Generations killed off Captain Kirk, William Shatner was back as Kirk — on Futurama. The classic Futurama season 4 episode "Where No Fan Has Gone Before" reunited the cast of Star Trek: The Original Series (except for James Doohan as Scotty).
Technically, William Shatner plays himself, or more accurately, the head of William Shatner, and the rest of Star Trek's actors also play their own severed heads. When an obsessed fanboy alien named Melllvar orders the Star Trek actors and Planet Express crew to indulge his fantasies, the Star Trek legends get their bodies back.
William Shatner is absolutely hilarious playing himself, playing Captain Kirk, even preemptively tearing his own shirt and making out with Leela (Katey Sagal). Futurama's "Where No Fan Has Gone Before" is a loving ode to Star Trek, and William Shatner and his fellow Starship Enterprise legends came to play.
2 Star Trek IV: The Voyage Home

Star Trek's first three movies were serious business, dealing with the meaning of existence, friendship, old age, death, and resurrection. Director Leonard Nimoy chose to lighten things up in the bright and cheerful Star Trek IV: The Voyage Home, and William Shatner was the brilliantly comedic head of the spear.
Star Trek IV is a brilliant showcase for William Shatner's fast-talking, double-taking comedic strengths. Admiral Kirk and the crew of the Starship Enterprise may be a bunch of fish out of water in 1986 San Francisco, but William Shatner was in his element as the film's humorous center of gravity.
From scolding a driver who almost ran him over with "a double dumb-ass on you!" to Kirk's slapstick banter with Spock, to the Admiral asking whale biologist Dr. Gillian Taylor (Catherine Hicks) to help them over pizza and beer, William Shatner gives his most endearingly funny Star Trek movie performance in Star Trek IV.
1 Star Trek: The Original Series – “The Trouble With Tribbles”

After peppering humorous moments throughout its first two seasons, Star Trek: The Original Series delivered the franchise's first true comedy episode in "The Trouble With Tribbles," and it endures as an all-time classic almost 60 years later.
William Shatner's Captain Kirk set the gold standard for Star Trek comedy in "The Trouble With Tribbles." Star Trek: Deep Space Nine's remake and homage, "Trials and Tribble-ations," shows Captain Kirk's hilarious tribulations from a different angle as DS9's heroes pose as part of Star Trek: The Original Series' crew.
