More from EW
1 of 11
APPLE PICKING WITH MR. T
Conan was often at his most inspired when he left the confines of the studio and unleashed his wackiness upon the world. And the always-game Mr. T was the perfect road buddy for this trip to an upstate New York apple orchard. No one shouts intimidating threats at fruit better than Clubber Lang.
2 of 11
IN SEARCH OF...IRISH O'BRIENS
It's hard to tell how much Conan had to drink on his trip to Ireland looking for his roots — there was clearly beer present, but he's so damned loose as a matter of course — but watching him sing and dance and drink with scores of passersby makes me wish he'd just do a travel show.
3 of 11
TEXAS THUNDER, PART 1
Don't you wish you had a lever sticking out of your desk that played bizarro clips of Chuck Norris' Walker, Texas Ranger?
4 of 11
TEXAS THUNDER, PART 2
In the early years of Late Night, back in 1997, Conan went deep in the heart of Texas — to Houston, where his show would only air at 2:40 am — to find out who, if anyone, was watching. Few things are funnier than seeing a giant redhead scour all-night joints looking for people who might recognize him.
5 of 11
HOT IRONS AND THE STRIKE
With his writers unable to work, prohibited as they were by the Writers Guild of America's strike, O'Brien launched into a series of fantastically off-kilter stuff. He'd spin his wedding ring on his desk, just to see how long it'd go; he gave a fan a tour of NBC Studios; and routinely badgered his exec producer Jordan Schlansky, who showed off a frightening talent with the bullwhip.
6 of 11
In the words of Conan himself, ''This fellow combines the classic sensibilities of a 1950s robot with the dynamic flair of a 1970s street pimp.''
7 of 11
STAREWAY TO HEAVEN
Nothing was quite as randomly bizarre as the staring contests Conan would hold with his once-and-future sidekick, Andy Richter.
8 of 11
Back in 2002, Conan hit the Winter Olympics in Salt Lake City...with his ass. See, he wanted to become a speed skater, going so far as to recruit a former Olympic champion, Dan Jansen, to give him some tips. None of which helped. At all.
9 of 11
NAKED ANDY RICHTER
Really, how much more needs be said? (By the way, Matt Lauer is, clearly, unflappable.)
10 of 11
THE FUTURE, CONAN?
While there have been plenty of people to sit on Conan's couch, wield a flashlight, and don the velvet smock, none have been as routinely hilarious as Richter. (William Shatner comes in a close second.)
11 of 11
BONUS: TRIUMPH ON LINE FOR STAR WARS
Conan himself wasn't in this bit, but it is legendary. Triumph the Insult Comic Dog lived up to his name, ridiculing a collection of hapless geeks as they waited on line, days before Star Wars: Episode II opened. Pointing to a would-be Darth Vader's array of buttons on his ''armor'': ''Which of these buttons calls your parents to pick you up?''
(For more highlights of Conan's abbreviated stint at 11:35 p.m., see Conan O'Brien on Tonight: 10 great bits on PopWatch.)