“It’s very rushed, very hurried,” he says. “You’re doing one every single night. The disadvantage is that not everything is going to work. But you can try it again and again.”

And it is that freedom to craft his work, night after night, that O’Donnell relished about his time at the “Late Show.”

Have Jokes, Will Travel

O’Donnell currently lives on New York’s Upper West Side, six blocks away from his twin brother. The two are still very close, and have shared in their successes over the years.

Mark O’Donnell, who is a novelist and playwright, says that the life of a writer is like “a gypsy path”—where the wagon keeps rolling from one job to the next.

Indeed, O’Donnell spends a decent amount of time in California, where he has been working for the past six months on “The Downer Channel.”

This nomadic lifestyle has left O’Donnell little time for anything else, including starting a family.

“Everything worth doing seems to involve some sacrifice,” he says. “I myself have not had a family, which I guess is a regret for me. I would love some bawling, sloppy youngsters.”

O’Donnell was once married to a woman he describes as a “smart, funny, musically brilliant Sarah Lawrence grad.” But though he says that she always made him laugh and still does, they were simply “temperamentally and emotionally incompatible.”

There was also a woman that O’Donnell says he should have married but didn’t, a mistake that troubles him to this day.

“The useful message to you all might be to bravely go with your heart always and everywhere,” he writes in his 1976 alumni book submission.

Twenty-five years, four Emmy awards, and one near-death Alka-Seltzer suit experience after graduating from Harvard, O’Donnell seems to be doing just that. He’s found the work he loves, and though there have been plenty of bumps along the way, he’s laughing all the way.

—Staff writer Kate L. Rakoczy can be reached at rakoczy@fas.harvard.edu.