You wouldn’t know it to look at him, but Andy Richter is surprisingly fit. We’re hiking Mount Hollywood in LA’s Griffith Park and at least during the first mile of our trip, it’s been all uphill. But Richter is keeping a steady pace and even seems to be enjoying the climb. It’s a pretty impressive feat for a man whose body could be best described with adjectives like “chunky” and “rotund.”

Andy

“I’ve always been very bull-like,” he tells me. “I’m like the Vikings. They didn’t attack villages with screaming raids. It was just a slow climb forward, swinging a battle-axe with one hand like a farm thresher of killing. That’s exactly what I’m like. I’m a locomotive with the breaks off.”

I smile and try to pretend that I’m having nearly as much fun as he is. But I’ve never been more miserable. I’m gasping for air, my chest feels like it’s on fire, and my thighbones are threatening to snap like stale breadsticks. And worst of all, it’s entirely my fault. I’m the one who came up with this harebrained scheme in the first place. I thought it’d be hilarious to watch a doughy man like Richter try and climb a mountain, especially because his regular gig on The Tonight Show rarely requires more physical exertion than making the occasional bon mot. But my plot backfired. I feel like an asthmatic trying to keep up with a marathon runner.

You don’t need to spend long in Richter’s company to realize he’s not always what he appears. He’s got the soft, friendly features of a Midwesterner — he was born in Michigan and raised in a small town just an hour outside Chicago — and his demeanor is affable and laid-back. He seems like the sort of guy who’d be the cut-up at a church social or his suburban neighbor’s barbeque. He’s certainly not somebody you’d expect to wear a skin-tight half-shirt with “LICK” written across the chest, or cheat in a staring contest by convincing his competitor’s grandparents to strip. But that’s exactly what he was doing for much of the 90s, when he served as Conan O’Brian’s sidekick and comedy cohort on the Late Night talk show, a post he held for eight years before retiring in 2000.

Richter notices that I’m straining to keep up with him and he slows down in a show of fat guy solidarity. “I’ve never been one to enjoy cardiovascular exercise for its own sake,” he says, as if apologizing for being too enthusiastic about fitness. “Which I guess is like saying, ‘I’ve never been good at staying alive longer.’ I am totally from the school of, ‘Well, there are people worse than me.’ That’s what I cling to. ‘Well I’m not that bad.’ Yeah, but you’re still pretty fucking fat.

“It’s ridiculous that I’m this out of shape,” he continues. “Especially given the line of work I’m in. I’ve never watched anything I’ve done. I just don’t give a shit. Because I know the big fucking lump of soft-serve vanilla human flesh that’s in the middle of the frame.”

Luckily for him, washboard abs aren’t a big prerequisite for comedy. But you can’t blame the guy for being a little self-conscious. It’s been a very public summer for Richter, what with his fancy new job and all. Now that his old boss from Late Night has taken over hosting duties for the Tonight Show, Richter has staged a triumphant return to late night TV, joining the show as Conan O’Brian’s official… something.

Even Richter is unclear on his exact job description. “I’m an announcery, side-kicky cast member kinda thing,” he says. “I don’t know how else to describe it. It’s a fucking talk show and he’s the host and he talks to me and I talk to him and I do comedy bits. I’m just kinda there to lighten the load. Otherwise it’d all be about Conan and nobody wants to see that.”

Richter and O’Brian, who’ve worked together in some capacity since 1993, have a complicated relationship. They’re a comedy duo first and foremost, but it comes with shades of codependence. Richter describes their partnership this way: “When transporting a show horse, like the kind that’s trained to perform in a circus or a rodeo, they frequently put another animal in the horse trailer, like a dog or an old goat that nobody cares about, to make the horse feel calm and secure. I kinda feel like that’s my job. I’m the old goat that keeps the star horse company so he doesn’t get agitated and kick down the door off his stall.”

It’s a joke, but a joke with a grain of truth. “He does tend to worry,” Richter admits of his TV partner. “He gets so wound up sometimes that he needs to be told to have a good time. There’s something about Irish-Catholic guilt, second only to Jewish guilt, that’s pretty strong. It’s so free-floating and doesn’t even have a point. I used to have conversations with him where I was like, ‘Please, enjoy this! My god, the fruits of your labor are bountiful!'”

O’Brian isn’t the only one who finds Richter a calming presence. Although he’s dressed like a prepubescent boy (he’s wearing a baseball cap, shorts and a t-shirt with a cartoon character drawn across the chest) and he has the pale complexion of somebody who rarely ventures outdoors, I feel perfectly safe letting him assume the role of hiking guide. He exudes an air of confidence even when he obviously has no idea what he’s talking about.

He explains to me the realities of LA’s wilderness — “It’s all built on risers,” he says. “If the bank crisis should deepen, all of this will be rolled up and taken away” — and points out the predominance of single male hikers — “Is this the place in the park where a fella goes if he wants a blowjob from another fella?”

He even finds a way to assure me that, should we encounter a pack of hungry lions, we have nothing to fear. He does this by sharing a long story about his first experience walking through New York’s Central Park at dusk. “My friend and I didn’t know how to read the map so we just kept walking and walking,” he tells me. “We ended up going something like 60 blocks, and when we finally left the park it was dark and we were in Harlem. But we weren’t scared because we convinced ourselves that everyone would think we were cops. I guess because we were fat and wearing leather coats. We looked like off-duty cops.”

Logically, I know this doesn’t really apply to us, unless he’s suggesting that mountain lions might mistake us for two overweight cops and somehow be intimidated by that. But for some reason, it still puts me at ease. Richter is just that convincing.

In keeping with his fearlessness, he’s undaunted by expectations surrounding the “new” Tonight Show. The only hint of trepidation is his relief that they’ve stayed away from Jay Leno’s turf. “I’m glad we get to shoot our show in a different building,” he admits. “It would be weird to do the Tonight Show from Jay’s set. It’s not like there are hard feelings or anything, but it just makes it that much easier to feel like we’re doing something different. If we took over his studio in Burbank, we’d probably need to burn sage.”

Instead, he and Conan have found their TV home at Universal Studios, which he explains is “like the Vatican. They have their own city, and I’m pretty sure I can legally commit murder on Universal property. That’s why I took the job, because I can have people killed. As long as they’re in Universal City, it’s fair game.”

Does that mean The Tonight Show will be ruled by marital law? “Law doesn’t play into it,” he says with a cryptic laugh. “It’s purely a flexing of bone-crushing power. At Universal, they’re very, very liberal about their murder.”

We reach the summit, and it almost seems worth the excruciating journey. Los Angeles is laid out before us in a stunning panorama. “At least from a distance,” Richter says, “this city can be quite beautiful.” We stand there is silence for a minute, just admiring the view, and then Richter wanders towards a ledge to take a leak. I try to step away and give him some privacy, but he waves me over.

“Don’t worry about it,” he says, his urine stream aimed squarely at the skyline of Hollywood.

It’s weird to carry on a conversation with somebody — especially somebody with Richter’s celebrity clout — while he’s holding his cock. I’m not sure whether to make eye contact or avert my gaze, just to make it clear that I’m not trying to check out his package. (I did check it out, by the way, and it’s impressive.) I wonder if I should join him, just whip out my penis and start pissing right next to him, so he doesn’t feel awkward. But I’ve got performance anxiety and I’m pretty sure that the best I could manage is a sad, insubstantial tinkle that’d just splatter Richter’s leg.

As he finishes pissing, he gives me a tour of his adopted home town. He points out various neighborhoods in Los Angeles and gives me bullet point factoids about each of them. Silverlake, he says, is filled with “fucking hipsters in their fucking fedoras riding around on bikes without breaks.” Hancock Park, where he currently lives with his wife and two kids, is “the second step on the white flight trail.” There’s downtown LA, which he visits frequently “because for some reason my children love all things Japanese.” And don’t forget Beverly Hills, which apparently is populated solely by “strange lizard-creatures and creepy old women with huge, tight tits.”

Maybe it’s all the endorphins from the climb or the lack of oxygen in our brains, but we’re both starting to get loopy. I can’t take my eyes off some nearby bushes, which are rustling so violently that I’m convinced we’re about to be attacked by rabid cougars. And Richter is getting misty-eyed as he waxes nostalgic about his favorite LA coffee shops.

“One of the nice things about this town is that the climate keeps things from falling apart like they do everywhere else,” he says, a large grin overtaking his face. “So you can find these old lime-green coffee shops with fifty coats of paint on the booths. I just love that. I find it tremendously comforting. Old shitty coffee shops remind me of when I was a little kid, eating with my grandparents.”

We notice a few hikers walking past us and continuing up another trail, and it occurs to us that we’re not actually on the mountain’s peak after all. “You’re fucking kidding me,” Richter groans. “There’s more? I don’t think I can do that. I’ve already got a splitting headache.” I find this reassuring, if only because it proves that Richter is human. And, like me, he just might be on the verge of a stroke.

We briefly consider resuming the climb before thinking better of it. “This is fucking far enough,” Richter declares, dismissing the uphill slop with an angry wave. “We get the idea.”

We begin our slow descent down the mountainside, both of us still a little lightheaded from the altitude. We’re giggling like teenagers who’ve been doing whippets behind a convenience store. “When I left, I ripped the guts out of that show,” Richter says of his departure from Late Night in 2000. “Thank god I came back. You’re welcome, America.”

He’ll play the part of an egomaniacal prick for a laugh, but Richter actually couldn’t be more grateful for The Tonight Show. “I’ve been shitting solid turds of relief ever since getting this job,” he says. “Especially now, in this economy, I’m just so fucking happy to have a regular job.” The past decade has been hit or miss for Richter. He’s starred in critically lauded but largely unwatched sitcoms like Andy Richter Controls the Universe and Andy Barker, P.I., and what-the-hell-was-he-thinking fare like Quintuplets and the Olsen Twins’ flop New York Minute. When he says he’s just happy for the steady work, he’s not being facetious.

“I had a lot of ambitions when I left the show,” he says of Late Night. “I wanted to do my own things and try something different. I wish I’d been more productive. I should’ve tried to write more of my own material. Most of the things I’ve done, it was usually somebody else who built it and said, ‘Hey, come in here and help us run this ship.’ But I didn’t do enough of it myself. I didn’t design any big ideas from scratch, which I think was just garden variety insecurity and fear.

“Now I feel like, okay, I gave all of that a shot and it was great, but I miss the smallness of doing a late-night show.”

I point out that he’s probably the first person ever to describe The Tonight Show as “small”.

“I don’t mean small in terms of scope,” he says. “I mean the immediacy of it. Anywhere else, if I’ve got an idea, I have to go out into the world and try and sell it. But here, if I’ve got an idea, I can put it on TV tonight.”

Not that he thinks it’ll be that easy. He may be a veteran of late night comedy, but NBC isn’t giving him creative carte blanche. “I can’t go out there and say ‘screw the establishment’ or ‘suck on this, old man!’ That’s not The Tonight Show. Hopefully we’ll be able to do stuff that’s just as weird and funny as some of the things we got away with on Late Night, but this is a very different show. You don’t drop the f-bomb when grandma comes over.”

He promises that the Andy Richter we loved on Late Night — who wouldn’t think twice about streaking through the Today show set or predicting his eventual cross-over into gay porn with 69 on the Richter Scale — won’t be completely tamed for the earlier time slot. “If I whine enough, I can probably do whatever I want,” he says. “Trust me, Conan doesn’t want to hear me whine.”

Although he won’t be specific, he promises big surprises on The Tonight Show this summer. “I don’t want to guarantee anything,” he says, “But there’s a pretty good chance that I’ll have a better parking space on the Universal lot by July. That’s gonna make a big difference to the quality of the show. Maybe not in ways that are necessarily visible, but it will matter. There’ll be a certain lightness and contentedness to me.”

Richter suddenly grows quiet and motions for me to lean in close. “Look at that guy over there,” he whispers. I follow his gaze and see a short, middle-aged man standing next to a cliff. He’s holding what appears to be a deflated pink Teddy bear, and he’s attempting to ram a mangled coat hanger into its open belly. It’s unclear whether he’s stabbing the bear or trying to fix it, but either explanation is equally troubling.

I suggest walking over and asking the man for details, but Richter refuses. “No, no, no,” he whispers sternly, continuing down the hill without me. When Pink Teddy Bear Guy is out of range, he explains his reservations. “I just didn’t want to ruin it,” he says. “The truth would’ve been boring. I’d rather keep it within my own paranoid fantasies.”

I’d never have taken Richter for the bashful sort, especially when so much of his job involves interacting with strangers, sometimes crazy-looking strangers on the street. “Yeah, doing those segments for the show can be tedious and feel the most like work,” he admits. “For me at least, there’s nothing fun about walking into a crowd of people and saying, ‘Hey everybody! Look at me and listen to me and talk to me!’ I have a natural aversion to that.

“Any time I do a remote, there’s a moment of…” he lets out a long and miserable sigh… “‘Ooooooh boy, this is going to be the worst thing eeeever.’ You’re going out, you’re talking to strangers and putting a microphone in their face and trying to make comedy and wondering how the hell it’s all going to fit together in the editing room. It’s torture.”

Richter slows down to a crawl, squinting towards the horizon. “I don’t recognize any of this,” he says, turning around to study our path. “Are you sure we’re going the right way?” I have no clue. I thought it was understood that I’ve been following him. I’m not comforted by the lack of other hikers on this trail, or the sudden appearance of signs that read: “Caution: Rattlesnakes.” (“At least we’re doing something rugged,” he says. “That sign wouldn’t be nearly as cool if we were just playing golf.”)

Richter seems to sense my uneasiness, and he tries to assure me that despite his utter lack of experience surviving in the wild or even camping as a kid, he is somehow qualified to get us out of this mess.

“I’ve watched enough TV to figure it out,” he tells me. “We just have to go downstream. That’s what they always do when characters get lost in the forest. And it makes sense. It’s gotta be better than upstream, right? Civilization’s eventually going to show up at the end of a stream.”

We look around but there’s no river, no stream, no indication whatsoever of any flowing body of water.

“Or we just keep walking and hope for the best,” he says with a shrug.

At that exact moment, as if on cue, a coyote steps out of the brush and onto the hiking path, pausing to glare at us. Its eyes are yellow and unblinking, and it looks like it’s considering whether we’re worth the trouble. I cower behind Richter, because this seems the most logical response to confronting a fanged predator on a deserted stretch of mountain.

“Woooow,” Richter says, without even breaking stride. “Look at him! He’s so fat!”
The word “fat” hangs in the air. The coyote tilts its head, as if trying to decide if Richter really said what he thought he’d said. And then he turns and runs away, disappearing back into his mountain home or wherever coyotes go when they’re not stalking hikers.

“What a pretty creature that was,” Richter says, but it’s too little too late. I explain my theory, that he likely scared away the coyote by making it feel insecure about its weight. This is California, after all, where every living thing has body issues. Richter just laughs at me. “I didn’t mean fat as an insult,” he insists. “He just looked… well-fed.”

We walk in silence, but I can tell it’s still on Richter’s mind. He finally turns to me and says, “Maybe I should go back and apologize.” He has a terse smile that suggests it’s not completely a joke.

But at that point, it’s too late. We’re back on the right trail again, walking alongside weekend hikers and single men looking for anonymous sex and at least one guy clutching a pink teddy bear, all of us stumbling down the hill towards Los Angeles.

(This story originally appeared, in a slightly different form, in the October 2009 issue of Playboy.)