Indeed, they're big shoes to fill. Good thing Conan O'Brien reportedly wears a size 12 and a half.
In his first stint as the host of "The Tonight Show," the former "Late Night" host lived up to the legacy of Jay Leno and the rest of the household names who've held court at 11:30 p.m., staying true to his own brand of awkward humor while honoring the "Tonight Show" franchise.
After a montage that showed him running across the country, from his former New York City digs through Chicago's Wrigley Field, past the Rockies, under the famous Las Vegas sign before finally reaching Los Angeles, O'Brien arrived in his studio to raucous cheers. Attempting to quell the crowd, he cracked, "Well at least we know the applause sign works."
O'Brien's still as self-depreciating as ever. "I'm on a last place network, I moved to a state that's bankrupt, and tonight's show is sponsored by General Motors," he joked later in his monologue.
He waited until after a segment that showed him hijacking a tram tour of his new workplace, Universal Studios, to nod to his predecessor. O'Brien called Leno "a man who took very good care of this franchise for 17 years ... a very good friend" and said he's looking forward to Leno's new prime time show being his "lead-in once again."
Once his first guest came out, the show took a tone from familial back to familiar O'Brien territory.
"No one thought you could do it, not one person," said Will Ferrell, on the show to promote his new movie, "Land of the Lost." "And you're here."
O'Brien joins a long list of public figures charged with taking on a seemingly larger-than-life legacy. Some slide into well established roles with style and grace; others skid and end up with a foot in their mouth.
Like O'Brien, Leno took a similar "put your own stamp on it but don't screw it up" approach when he inherited "The Tonight Show" from Johnny Carson in 1992.
"I like to look back at the history of hosts and say, 'Gee, it's my turn not to drop the ball,'" Leno told The Los Angeles Times in 1991. "It's like being given the crown jewels. You hold on to them and make sure nobody steals them. Then you pass them on to somebody else."
Sometimes the jewels seem so precious, the chosen handler perishes the thought of tarnishing them. That's how Drew Carey felt when CBS offered him the job of hosting "The Price Is Right," which belonged to game show legend Bob Barker for 35 years.
"If you think I'm going to sit at 'The Price Is Right' so everybody can take potshots at me, forget it," Carey thought when CBS first approached him. But, the comedian told The Associated Press in 2007, the network's persuasion plus the endorsement of his friends and advisers convinced him he could take the reins from Barker.
"It's like meeting the right girl," he said prior to his debut. "This is a really good fit. I'm really comfortable here and it seems like I should have been doing this a long time ago."
While Carey opts for more audience banter than Barker did, interviewing them about their livelihoods during the show instead of reserving questions for commercial breaks, he made a decision when he accepted the job that he would preserve the old host's closing line: "Have your pets spayed or neutered."
"It's a tradition," Carey said. "It's been here all this time. I don't want to get rid of that."
Transitions aren't always so smooth. When Deborah Norville took over Jane Pauley's post on the "Today" show in 1989, she did so under a wave of speculation that her good looks and youth forced NBC to oust Pauley from her anchor chair too early. Viewers flooded the network with thousands of outraged phone calls and letters following the announcement that the then 39-year-old Pauley was ceding her spot to Norville after 13 years.
''If I'd been a 31-year-old man going on as news anchor, there wouldn't be nearly as much ink about this," Norville told The San Francisco Chronicle in 1989. "Are we saying that women can't share the same masthead on a publication or work in a law firm together? It's out-and-out sexism, and it denigrates the years I've spent trying to grow as a reporter."
''Jane and I are friends and, when you know the real story, it hurts to see the way it was depicted," she added.
For better or for worse and luckily for O'Brien, audiences seem to be more open to change when it comes to leading men and late-night TV. What follows is a comparison that O'Brien -- who depending on the day, likens himself to a leprechaun, a little girl and the female president of Finland -- would find laughable. Nevertheless: taking over "The Tonight Show" is kind of like becoming the new James Bond. Both gigs come with a sidekick (sure, Bond's are better looking), a killer wardrobe of suits, and of course, large legacies to live up to. Replace Sean Connery's name with Johnny Carson's and Pierce Brosnan's tale below rings true for O'Brien:
"I remember [Sean] Connery walking that walk more than 20 years ago," Brosnan said in 1995, on the eve of the release of his first Bond movie, "GoldenEye." He told The Orange County Register: "It's not something an impressionable young lad forgets, and Connery indeed casts a long shadow on this role. But you arrive on the set and you have to walk the walk. You can't think about Connery or [Timothy] Dalton. There's no getting away from it; you just have to do it. You have to trust yourself and know that you can do it. You're the man now. You're James Bond for a new generation."
ABC News Research's Melissa Lenderman contributed to this report.