Ten Great Moments in Conan O’Brien History

Conan O'BrienConan O’Brien is returning to television tonight with his new talk show, appropriately titled Conan, and to celebrate we decided to look back at some of our favorite moments from his years on Late Night with Conan O’Brien and The Tonight Show.

While this list could probably go on well into the hundreds, we decided to limit it to our ten favorite.

In the Year 2000

One of our favorite bits from Late Night was when Conan would take a look into the future and tell us what the year 2000 is going to be like. When the sketch first premiered, Conan and his sidekick, Andy Richter, always performed it. After Andy left the show, Conan would bring on actors and comedians to share his psychic visions. Awesomely, even after the year 2000 came and went, they still performed the skit regularly and still referred to “In the Year 2000″ as a look into the future.

The Masturbating Bear on Million Dollar Giveaway

When NBC was trying to cancel Late Night, no one was more supportive of his boss than the Masturbating Bear. You know, before Conan’s show, bears that like to openly pleasure themselves never had a place on television. But not only has the Masturbating Bear been accepted, he’s beloved.

In this legendary skit, the Masturbating Bear is picked from the audience to be a contestant in a money booth. Everyone knows exactly what’s going to happen when the money booth starts up, but it’s still hilarious when it happens.

SAT Analogies

We were in high school when Conan debuted his SAT analogies segment, so we’re guessing that he’s the one responsible for our community college educations, Mom. But we did learn something valuable from these sketches, and that’s that you can take some of the simplest things (SAT analogies or, say, a list) and make a living doing it over and over again in a less traditional way. Ahem.

Norm Macdonald Hits on Courtney Thorne-Smith

Part of the magic of Late Night, especially in its earlier years, was the hodgepodge of guests that Conan would have to talk to. By the end of any given show, Conan and Andy were always the bread in an awkward C-/D-list celebrity sandwich. The best example of this is also one of the funniest things we’ve ever seen on television ever: Norm Macdonald simultaneously hitting on and making fun of Courtney Thorne-Smith while she plugged her new movie. For better or worse, you never would have seen this go down on Letterman’s show.

Max Weinberg on Britney Spears

Jimmy Fallon scored big time when he landed The Roots as his house band, but we still think that Conan’s Max Weinberg 7 is the best. All you really need in a talk show band is a group of people who can throw together a rousing 10-second version of “Build Me Up Buttercup” two hours before the show tapes, but with Max we always got much more. Max won’t be joining Conan on his new show due to heart problems that the drummer has said were only worsened by last year’s cancellation/Leno drama. Damn you, Jay Leno.

If They Mated

One of Conan’s most popular segments was “If They Mated,” a twisted Photoshop experiment that took two celebrity’s faces and blended them together to show us what their offspring would look like. The result of two attractive people’s faces being mashed up was always one of the ugliest and physically revolting things we’ve ever seen and is most likely responsible for those reoccurring nightmares we had in the early 00s.

Max Weinberg’s Public Service Announcements

In a parody of NBC’s long-running “The More You Know” series of celebrity public service announcements, Max Weinberg would spit worldly advice in ten to fifteen second increments that were so hilarious they ended up being the highlight of many an hour long episode. Our favorite by far is the one posted here, where Max Weinberg sets the ladies straight on the risks associated with using condoms. But it was a tough decision choosing just one, here are a few more that are just as great…

Max Weinberg on Hookers and Marriage

Max Weinberg on Impotence

Max Weinberg on Gun Safety

New State Quarters

Back when the treasury decided to release official quarters for each state in the union, they probably never realized that they were setting most of the country up for a series of jokes at their expense. By staggering the release of the quarters, they left everyone plenty of time to speculate as to what the state quarter of say, New Jersey for example, was going to look like.

In this famous skit, Conan reveals that New Jersey is the only state willingly given up by the Indians, among other dead-on observations.

The Walker Texas Ranger Lever

Through some assuredly unholy merger that is probably still destroying television as we speak without us even knowing it, NBC somehow acquired the right to show clips of Walker Texas Ranger without paying any royalties.

Once the news broke, Conan did the only thing a person could be expected to do in a situation like that. He had a lever installed next to his desk that showed cheesy clips from the famous Chuck Norris cop drama on-demand. Hilarity ensued.

Shopping on Rodeo Road

Clips from Conan’s Tonight Show days are scarce, so who knows how this one has survived this long on YouTube (or how long it will remain there). But we’re happy to see it again.

In this segment from the earliest days of his stint hosting the most famous late-night talk show in all the land, Conan is shot down after requesting a shopping spree on Rodeo Drive in Beverly Hills to be financed by his new bosses at NBC. By way of a compromise, they send him shopping on Rodeo Road in South Central Los Angeles instead.

Let this be just another reminder of the type of hilarity we’ll probably never see on The Tonight Show ever again. But at least Conan is back on the air now.