The comedy industry is hard to navigate. Between the difficulties of breaking into show business, the thin line between edgy and insensitive material and the likes of Dave Chappelle and Amy Schumer giving comedians a bad name, comedy is a daunting facet of the entertainment business. Few comedians have traversed this minefield of an industry as well as Conan O’Brien.
One of O’Brien’s greatest strengths as a comic is the long-fostered intellect behind his humor. The Boston-born comedian graduated high school as valedictorian and studied history and literature at Harvard University. Before graduating from the Ivy League school in 1985, O’Brien served as president of The Harvard Lampoon, the university's undergraduate humor publication.
By 1988, O’Brien was working as a writer for Saturday Night Live. During his three years at the sketch comedy show, O’Brien created a number of recurring characters and wrote some of the show’s classic sketches. In these early days, he asserted his comedy style of taking simple premises to hilarious heights by his attention to detail and flawless wit.
In 1991, O’Brien left 30 Rockefeller Plaza without a clear path in front of him. Around this time, the showrunners of “The Simpsons” called O’Brien and offered him a writing job on the popular animated show.
“‘The Simpsons’ was sort of notorious at the time,” O’Brien said in an interview with Vanity Fair. “Everyone wanted to be on that show, but they never hired. I think they were still going off the original crew.”
This stroke of luck and early testament to O’Brien’s gift for comedy led to a short but revolutionary stint writing for “The Simpsons.” After a few years, David Letterman announced his departure from “Late Night” and O’Brien was selected to replace him as the show’s host.
Due to the paradoxical intersection of O’Brien’s awkwardness and his intelligence, exacerbated by his lack of experience in the public eye, his iteration of “Late Night” was slow to earn positive critical reception. However, the comedian came to embrace this characterization and it became a staple of his style. His synthesis of wacky and intellectual humor, as well as his comical self-awareness, allowed him to continue hosting for a decade and a half and earned him the top spot on IMDb’s ranking of the top 40 late-night talk show hosts of all time.
After hosting “Late Night with Conan O’Brien” from 1993-2009, the host continued his residence in the world of late-night television until 2021. He went on to host “The Tonight Show” for less than a year and then created “Conan,” his own show featuring remote travel segments titled “Conan Without Borders.” After the COVID-19 pandemic, O’Brien left late-night TV and made his podcast, “Conan O’Brien Needs A Friend,” the focal point of his professional work.
“After 25 years at the Late Night desk, Conan realized that the only people at his holiday party are the men and women who work for him,” reads a description of the podcast on the TeamCoCo website. “Over the years and despite thousands of interviews, Conan has never made a real and lasting friendship with any of his celebrity guests. So, he started to do just that.”
The podcast is a perfect union of O’Brien’s humor and interviewing style. His journalistic background in high school and college aided O’Brien while hosting late-night television, and those skills shine as he crafts interesting conversations with impressive people, all while tapping into the hallmarks of his comedy: absurdity and self-deprecation.
In early 2025, O’Brien hosted the 97th Academy Awards. His performance was provocative and hilarious, and he walked the tightrope of goading jokes with wit and delight, from poking fun at Karla Sofia Gascón’s social media presence to subtly addressing the realities of the current presidential administration.
In addition to being invited back to host next year's Oscars ceremony, the industry honored O’Brien with the Mark Twain Prize for American Humor on Sunday. In his acceptance of the award, O’Brien succinctly summarized all of the things that make him a true icon of comedy: “I accept this award in the spirit of humility, stupidity, inanity, irrelevance, fear, self-doubt and profound, unceasing silliness.”
Sophia Rooksberry is a junior studying journalism. Please note that the views and opinions of the columnist do not reflect those of The Post. Want to talk more about it? Let Sophia know by tweeting her @sophiarooks_.
