Conan O'Brien Previews His New Primetime Special and Takes Us Behind the Scenes of His Biggest Viral-Video Hits

From left: Conan O'Brien, Kevin Hart, and Ice Cube in TBS's 'Conan to Go'
From left: Conan O'Brien, Kevin Hart, and Ice Cube in TBS's 'Conan to Go'

Note: This is Part 1 of our conversation with Conan O'Brien; Part 2 can be found here.

He's survived two decades in the cutthroat world of late night TV, but this month, Conan O'Brien attempts something he's never tried before: TBS primetime.

"There have been many challenges in my life," O'Brien tells Yahoo TV, "but getting to TBS primetime has been the greatest."

His new one-hour special, Conan to Go (airing Dec. 18), collects the very funniest remote bits from all four seasons of his TBS talk show, Conan. (Yes, it's been almost five years since the infamous Tonight Show debacle; let that sink in for a minute.)

Related: Conan O'Brien on Becoming Late Night's 'Grand Old Man'

Whether he's learning street lingo from Kevin Hart and Ice Cube in a Lyft car or getting wine-drunk at the American Girl store, Conan's most celebrated adventures outside the TBS studio are all here, and they've all found a second life online — a concept O'Brien is still getting used to.

"For years, I would shoot a piece, and people would see it that night or not see it," he says. "Maybe they would catch it on the rerun. And then every five or ten years, we'd do a best-of show and people might see it there. Now people are always seeing it; 'I just saw it last night,' and you might have done it six months ago. But what's interesting is, it all finds the right people."

And having those two decades of experience under his belt helps, too. "I feel like I've learned some tricks over time doing these, and I'm really proud of them," he says. "They're some of my favorite things I've done in comedy… And it's a chance to see me without makeup. Which, let's face it, is every American's dream."

Here, we dig deep with Conan and get him to shed some light on three of his most popular video pieces:

"Ice Cube, Kevin Hart, and Conan Share a Lyft Car"

This clip of Conan taking Ride-Along stars Ice Cube and Kevin Hart on a tour of L.A. using the ride-sharing app Lyft was a certified viral hit, racking up more than 13 million YouTube views. One highlight is Ice Cube introducing Conan to the concept of "fowties," aka 40-oz bottles of malt liquor. And now Conan can't escape them.

"I get them as gifts," he tells us. "We have a small refrigerator in the garage and I ride bicycles a lot, so I've got some Vitamin Water Zero in there, and I also have, like, four 'fowties' in there… When anybody stumbles into my garage to get a drink and they open it and see, like, six malt liquor bottles, it doesn't look good. But it adds to my street cred. Or subtracts from it, I don't know."

Conan also takes some heat from Kevin Hart in the clip for his very tight skinny jeans, but he insists the teasing hasn't deterred him: "Kevin Hart has a lot of power in the business. I love Kevin. But when Kevin Hart tells me I've gotta stop doing something, I go the other way. So I had those pants tightened. I haven't felt my scrotum in about nine months."

Despite the clip's success, though, Conan says he's not looking to make a sequel: "In comedy, I hate doing things again. It's against my nature. I always think it would never be as good… What I like is to keep trying to find new combinations. I'm constantly trying to mix it up, rather than turning it into, 'Who am I going to go in a car with this week?'"

"Conan Visits the American Girl Store"

It's a little unsettling watching a grown man unaccompanied by a child visit this popular doll store, where girls can purchase accessories, take photos, and even share a fancy lunch with their dolls. (Yes, the dolls can order, too.) And Conan's not sure it's helped the company much, either: "I think their stock plummeted after that video came out."

He's joking, but Conan does go into full-on creep mode here, leering at a female employee and getting drunk on white wine in the store's restaurant. (With a doll by his side, of course.) He hasn't dared to go back since, either: "I think they do have my picture up, like someone who passed a bad check. You know, there's nothing creepier than having your picture up as a warning at an American Girl store. It's wrong in every single category."

The store did give him a doll to take home to his daughter, but she already had one, so he donated the new one to charity. Plus, he says, it just came with too many bad memories. "They all have their backstories, and her story matched mine too closely. You know, 'she transitioned from network to cable… she burns easily… her self-deprecating wit has…' No no no."

This clip got a big response from women viewers, O'Brien adds. "They really love that I sat there and got wasted on white wine. They say, 'That's exactly what I did!' All you can do to sort of counter the surrealism of watching a doll order 65 dollars worth of food is to quietly get drunk."

"Clueless Gamer: Conan Reviews Grand Theft Auto V"

This is part of the "Clueless Gamer" series, where O'Brien struggles to play the latest video games with help from his gamer pal Aaron Bleyaert. And it's not an act: Conan says as far as video game expertise goes, "I think I drop out at the Ms. Pac-Man level." His first crack at the notoriously violent GTA5 leads to him getting kicked out of a strip club and eventually stealing a helicopter to exact his fiery revenge.

"I'm very honest about the fact that I don't belong here," he says. "I shouldn't be playing these games. What's hilarious is, now there are meetings at massive companies that make billions of dollars an hour in Tokyo: 'We must have Conan rate this game!' And we always say the same thing: 'You realize, I have no facility with these games; I'm really gonna make fun of them." And they're like, "We understand! Please, we beg of you! We need your seal of approval!"

So what's next for Conan outside the studio? He's already cooking up his next idea, which he can't tell us much about: "It's gonna have to be heavily bleeped, that's all I can say. I think every third word will have to come out of it." And he won't be satisfied until he pays some sort of spiritual penance on one of these shoots: "I guess my dream is to be very badly hurt doing one of these things. It's a Catholic thing."

For Part 2 of our conversation with Conan O'Brien, click here.

Conan to Go airs Thursday, Dec. 18 at 10 p.m. on TBS; Conan airs weeknights at 11 p.m. on TBS.