Conan Has A Small Request While He Carves His Tombstone

By:
Conan Has A Small Request While He Carves His Tombstone

Conan O’Brien, along with most everyone who appears on his podcast, Conan Needs a Friend, lives a very charmed life – and he knows it. “I have absolutely nothing to complain about, and I would like that on my tombstone, which would be ironic, ‘cuz I’d be dead. Which is a legitimate thing to complain about,” the legendary late night host lamented on the most recent episode.

Fleishman is in Trouble star Lizzy Caplan joined O’Brien on the podcast this past week, wherein she and O’Brien talked about the strange dissonance between living a life of fame and fortune and still feeling uncomfortable in conversations with that one aunt who can’t help but cut them down for their choice in careers. Caplan and O’Brien observed the social reality that those who live public lives in film and TV have somehow given implicit permission for friends, family, and the occasional complete stranger to give unprompted, unrequested, and unfiltered feedback about their careers.

Caplan and O’Brien aren’t complaining about their lives as celebrities, they just wish people would save their snarky comments for Twitter instead of Thanksgiving dinner.

“Part of this journey of this podcast started with me just wanting to be very honest, if I would, talking to people who anyone else would envy and saying, ‘Yes, it is great, I’m not complaining, but, also, it is very complicated,’” O’Brien began. 

Caplan told O’Brien the story of her Thanksgiving and how her distant relatives revel in passive-aggressively panning her projects in order to prove that her entertainment career doesn’t impress them. “It’s always family friends, or like some distant aunt who’s like, ‘I saw that show. It wasn’t for me’ … I don’t go to your accountancy office and say, ‘You know, you’re just doing fine,’” said the actress.

O’Brien and Caplan are well aware that nobody wants to hear celebrities complain about the cosmically inconsequential inconveniences of being rich and famous. With that in mind, O’Brien has observed a phenomenon in which complete strangers will approach him to criticize his career out of this sense that they are entitled to knock him down a peg as some sort of payment for his ability to live his comfortable life.

O’Brien tries to practice patience with those who feel authorized to comment on his life and career to his face, but even he has a line – said the comedian, “It rarely happens, but the times when people are just being downright rude, I’ll say to them, ‘I do not expect you to treat me better than other people, but I do expect you to treat me as well as other people.’”

Not that he’s complaining. O’Brien makes it clear that no part of his gripes with the occasional insulting comment has diminished the gratitude he has for his unique life. Conan cracked the joke about his tombstone at the end of the talk of strange celebrity social interactions, adding on to the engraving, “How about, ‘Up until this point, I had nothing to complain about…' Conan O’Brien, 1963-2025.”

Said O’Brien’s assistant and co-host Sona Movsesian, “I have to fix up my resume.”

Sign up for the Cracked Newsletter

Get the best of Cracked sent directly to your inbox!

Forgot Password?