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“We probably won’t fall through,” Tom Green said as he stepped out onto an expansive frozen lake that sits along his bucolic 150-acre farm in the hinterlands of Ontario, periodically stamping his foot to be sure. I followed his lead, bundled in a polar-rated Baffin snowsuit he’d wisely insisted I wear for this expedition.

A few decades ago, this easily could have been a setup. He was, after all, a guy who became superstar famous for audacious pranks that captured the bubbling, cheeky rebellion of Y2K-era youth. But that absurdity was kept at bay that frigid Tuesday in early January. Green, 53, is not quite the same troublemaker who crawled around on the street, interviewing unsuspecting passers-by with a “piece of poo on a microphone,” as he did in one of his most memorable bits.

He’s since moved on from those high jinks, even as similar content has proliferated across screens. Social media has made it so exceedingly easy for everyone to try to stand out from the pack, Green said. “To a certain extent, it’s lost its impact.”

These days, suckling is out and nuzzling is in. “I love Fanny,” he said later, cozying up to a mule that is one of the many animals I saw him gently tending to as he found joy in the little details of farm life. The chickens, for instance, had been laying more eggs than he could keep up with so he’d been lining some up on a nearby fence for the crows to enjoy.

“To me, I thought the weirdest thing that I could do is get a farm and a mule,” he said. “That’s kind of what makes it fun for me is that this is ridiculous. Can you believe this? I’m riding a mule.”

Green is returning to the spotlight this month with a flurry of new projects for Amazon Prime Video, including “I Got a Mule!,” an aptly titled hourlong stand-up special premiering on Jan. 28. “Tom Green Country,” a charming four-episode reality show that follows Green as he gets his farm in order with the help of friends, neighbors and his parents, comes out Jan. 31; and “This Is the Tom Green Documentary,” which recounts his dizzying rise to fame, debuted Friday.

“People are probably going to be surprised that I’m not, like, completely crazy,” he said of “Tom Green Country.” “There’s a sort of a wholesome heartwarming thing to this — that I have a close relationship with my family, that I love animals, that I enjoy doing a lot of things that a great many people in the world enjoy doing, like getting out into the woods,” he continued as we rambled around the property in an A.T.V. with his rescue dog, Charley, and his fiancée, Amanda Nelson.

After 20 years in the Hollywood Hills, Green realized that there was a misperception hanging over him. “I’m not really a Hollywood guy,” he said. “I started to feel like I wasn’t being true to my authentic self.” So he moved back to Canada in 2021.

“Tom is actually really reserved usually and serious,” Glenn Humplik — his sidekick on “The Tom Green Show,” the straight man to Green’s madman — said in a phone interview. “He’s very analytical about every single comedy bit and thing that he does. It’s not just a primitive demonstration. He understands why something is funny or not. And it goes beyond just comedy — about life. He really reflects on things a lot. Maybe too much sometimes.”

‘It’s Not the Green Tom Show’

“The Tom Green Show” started in 1994 on Canadian cable access television, half talk-show fever dream and half on-the-street mischief. It moved to CBC Television and then to the Comedy Network before Green entered the United States in 1999 like a wrecking ball, cracking the perfectly polished pop ecosystem dominated by the likes of the Backstreet Boys, ‘N Sync and Britney Spears.

“The way it hit MTV just at the right time and the way that they blasted it out there,” he said, “to be able to, that quickly, permeate into pop culture in the biggest country in the world for media, I realized this is different.”

When Green released the video to his novelty track “The Bum Bum Song (Lonely Swedish)” in 1999, his fans inundated “Total Request Live,” MTV’s wildly popular vote-driven countdown show, and it shot to No. 1. After a week, MTV essentially forced Green to retire it from rotation. The show had prerecorded the following week’s episodes, which was antithetical to its premise, and the network hadn’t anticipated Green’s sudden rise. “I feel for 98 Degrees,” Green winkingly told Carson Daly, the host of “T.R.L.,” on air.

Back in those whirlwind few years, Green hosted “Saturday Night Live,” graced the cover of Rolling Stone, and had a high-profile relationship and short-lived marriage to Drew Barrymore. Oprah Winfrey invited him and his parents, Mary Jane and Richard Green, onto her show. He wrote and directed the 2001 film “Freddy Got Fingered,” which seemed to set a new standard for how much a movie could be reviled by critics.

Perhaps most enduring, he was enshrined by name in Eminem’s lyrics to “The Real Slim Shady,” a track from 2000 that helped cement the rapper as one of music’s biggest stars: “Sometimes I wanna get on TV and just let loose, but can’t, but it’s cool for Tom Green to hump a dead moose.” Eminem was referencing a segment that initially aired in the middle of the night on Canadian cable access to a handful of viewers before it was eventually shown on MTV. Green could never have imagined it would somehow define him.

“It’s like you’re driving down the road, you’re trying to make a show, you’re living in your parent’s basement, you’re just looking for anything to film, and all you’ve seen is trees for two days,” he said, recalling the fateful drive from Ontario to Vancouver. “And then you look out the window, and there’s this giant, beautiful animal that was unfortunately hit by a car.”

‘I’m Just Biting Tom Green’

Green has alternately been called groundbreaking or juvenile; avant-garde or disgusting; ahead of his time or out of his mind.

Today, it wouldn’t be a stretch to call him the father of cringe-core, acclimating audiences to the gleeful discomfort of bits taken too far for too long, clearing a path for comedians like Nathan Fielder, Sacha Baron Cohen and Eric Andre, and shows like “The Office” and “It’s Always Sunny in Philadelphia.”

Andre, whose Emmy-winning “The Eric Andre Show” ran intermittently for over 10 years, has repeatedly called Green an inspiration.

“People were always like, ‘Where did you get the idea for the show?’” he said when he was a guest on “Tom Green Live!”, a talk show that ran on TV from 2013 to 2014. “Then, just one day, I was like, ‘Oh! That’s from Tom’s show, Tom Green. Then I was like, ‘Oh, I’m just biting Tom Green.’ So thank you for your brain.”

As a teenager, Green’s brain was shaped by “Monty Python” and “Candid Camera,” Norm MacDonald and Richard Pryor, but mostly David Letterman, his idol then and now. When Green was asked to guest host “Late Show With David Letterman” in 2003 — a call viewers see him receive in real time in the new documentary — he is nearly in tears. He considers it a high point in his career.

Green started doing stand-up when he was still a teenager, but his first taste of fame came as a member of Organized Rhyme, one of Canada’s first successful rap groups. The group won a Canadian Music Video Award in 1992. Green soon shifted his focus to comedy, but being part of Ottawa’s underground scene that combined hip-hop, punk and skater cultures helped define his outlook at a young age.

“When you hang out at punk rock shows all the time,” Humplik said, “you and all your friends are in that scene, you have a good understanding of the kind of rebel attitude and the sort of anarchy-style behavior at that age, and that sensibility definitely landed itself into the show.”

Technology was also an obsession of Green’s since childhood, and later, inspired by these scenes, he started hitting the streets with a camera in tow, an uncommon sight in the 1990s.

“It caught that audience, and people loved it,” Humplik said. “And it was fun, and it was real. It wasn’t manufactured.”

A Blessing and a Curse

Pioneers don’t always get the credit they deserve, his mother, Mary Jane Green, told me. “I think he felt that. But he has this ability to reinvent himself as he goes. And every time he does, it seems to become something.”

That’s just a drawback of pursuing unproven ideas, Green said. Once proven, the money comes, along with people who want to mold their own version of it. “That’s happened several times with me,” Green said. “When something works, it gets repeated, you know?”

He is in part referring to “Jackass,” the MTV skater-boy prank franchise that MTV swiftly installed when Green’s show went on hiatus after he was diagnosed with testicular cancer in 2000. As Green recovered, a new batch of stars was minted. Some segments on “Jackass” were clearly inspired by what Green had done; a more critical assessment would be that they were copied.

“They were skateboarders, and we were skateboarders. But we were making fun of bro culture — maybe they think they were making fun of it, too — but they are actually bros,” Green said. “They are actually cool, like Johnny Knoxville’s a cool guy. I’m not cool.”

“But to see other people do the same bit, it, well — the hard part was thinking of it,” Green said. “The act of doing it wasn’t the weird part, thinking of it was the weird part.”

He says he holds no ill will toward the “Jackass” cast: He understands more than most how exciting it can be to get anything on the air. But it’s one of several instances where he hasn’t been able to capitalize like others have, especially financially. “Jackass” alone has had multiple feature films in addition to the show and its spinoffs.

“Look, I have done well, I’m doing fine,” he said, “but, you know, a billion-dollar franchise is a lot different than ‘The Tom Green Show.’”

Aside from “Jackass,” or the abundance of prank content that now populates YouTube and TikTok, Green is also referring to his early forays into streaming: He started uploading audio clips to the web around 1999, and by 2003 he was uploading and streaming video.

Then in 2005, Green began streaming shows and segments from the web-optimized TV studio he’d built in his living room, including what would become “Tom Green’s House Tonight,” “Tom Green Live!” and “Webovision.”

“I was always looking at where technology was leading, and I was going, ‘How can I use that to make some art with it?’” Green said.

“There was this kid called Justin.tv. He was doing it at the same time as me. He wore a camera on his head all day,” he recalled. “I was over at my house, I was doing a talk show in my living room. And then there’s these kids up in San Francisco, and they were putting video online. We all knew of each other. One became Twitch. Then one became YouTube. And then I’m here on the farm riding a mule,” Green said with a smile.

He interviewed celebrities like Pamela Anderson, Steve Carell and Flava Flav. One guest, Joe Rogan, credited Green with introducing him to podcasting and recently called his 2007 appearance on the web version of “Tom Green Live!” transformative.

“When you had me as a guest on, it changed the course of my life,” Rogan told Green on “The Joe Rogan Experience” last year. “I remember like lightbulbs just going off in my head like, ‘Why don’t I do this?’ The idea came out of you, man.”

“I wasn’t gate-keeping,” Green told me, as we stood in what he called the “swamp cabin,” a quaint structure that overlooked a frosty mire that he built with a friend.

“I was showing everybody exactly how to do it. I’d have comedians up there, and I’d say, ‘Yeah, this is how we do it. We plug this in here.’ I enjoy the fact that all of my friends and comedians that I like could now circumvent the frustrating process of having the only route to being able to express themselves on television was by going through a short list of corporations.”

Reflecting on a Legacy

Except for putting a cow’s head in his parents’ bed as they slept, a nod to “The Godfather” that didn’t go over well, Green doesn’t have many regrets, he said as we warmed up over Nanaimo bars and butter tarts in his 1857 farmhouse, the wood stove roaring.

More so there were choices he wish he’d been more thoughtful about, namely taking opportunities to show audiences that he wasn’t an idiot, he was just playing one.

“I have probably thought about it a lot over the years,” he said of showing up in character on the late-night circuit.

“The thing that I was maybe miscalculating was that my show was so outrageous that it probably would have been more interesting for me to have gone on the show and just sat back like this and talk and be myself,” he said.

He was overexposed, he realizes, especially to a lot of people “who probably weren’t seeking out weird television but now were being confronted by it.”

That naiveté would haunt him with “Freddy Got Fingered.” “This movie isn’t the bottom of the barrel,” Roger Ebert wrote in a scathing review. “This movie isn’t below the bottom of the barrel. This movie doesn’t deserve to be mentioned in the same sentence with barrels.”

At the time, the reviews crushed Green. “That was the first time where I really got sort of a pushback to the weirdness,” Green said.

“I thought that people would understand to a certain extent that, like, he’s trying to be crazy, he’s not actually crazy. He’s trying to be silly,” he said. “I assumed that people would sort of do the mental gymnastics of understanding.”

“These are good problems to have,” he went on. “Still, doesn’t make it any easier.”

Although Green has stayed a pop culture presence, he’s never fully recovered from the film in terms of mainstream success. And, perhaps bittersweet, “Freddy Got Fingered” is now considered a cult classic. It was even featured last year on the Criterion streaming service, a modern hallmark of a certain type of artistic merit.

As for his next prediction, well, he’s living it.

In 50 or 100 years, “cities may no longer be as relevant,” he said. “People may start to realize that there’s a lot of space. We’re all connected now electronically, so we don’t need to be all sitting on top of each other.”

He has plans to travel to the desert soon, to ghost towns in Texas and New Mexico, areas that fell on hard times when the railroads closed or the highways diverted past them. Some still have infrastructure in place, he said, and beautiful architecture. “Why isn’t there an app that gets a whole bunch of people together? And they go buy a town, refurbish these towns, and bring it back to life,” he asked. “All the people that want to get out of the city and want to spend less money.”

“A big new idea,” he laughed. “Now someone else can go make a billion dollars off of it.”