Dan O'Keefe '90 (Writer and Producer, The Tonight Show with Jay Leno,
The Drew Carey Show, Seinfeld, The League, Silicon Valley)

by Nicole Torres

Originally from New York City, Dan O’Keefe grew up in a writing family. Both his parents were writers; his mother was an English teacher and his father an editor for Reader’s Digest. He was not allowed to watch television growing up, but he humorously recalls, “I was allowed to swear as long as it was grammatical.” His two younger brothers are writers as well, and all three of the O’Keefe brothers have enjoyed successful careers writing for either Hollywood or Broadway.

While he has enjoyed substantial success as both a writer and producer, his path toward a writing career was not always so clear. “For a long time I wanted to be an actor. I actually trained for years and years, and they didn’t have a major at Harvard, and I was thinking, ‘No one in this place is ever going to make it as an actor.’ And then, of course, Mira Sorvino, Donal Logue, and Matt Damon [did].”

Although Dan’s initial focus was acting—he participated in five to six theater productions per year while at Harvard—Dan also knew upon enrolling at Harvard that he wanted to write, specifically for the Lampoon. But his path to the Lampoon took persistence. Dan recalls, “It took me three tries—three comps—to get on the Lampoon.” He elaborates, “I failed miserably twice. The first time I didn’t even make it past the first cut. The second time I made it to like the second cut, but then didn’t make it, and the third time I made it all the way.”

It is well known that being on the Lampoon often leads to and aids in the success of a writing career in Hollywood and elsewhere. Nonetheless, Dan notes that the most helpful thing about being on the Lampoon was the opportunity for practice and development it provided. “It would be absurd to say that in the comedy writing business and in Hollywood, going to Harvard and being in the Lampoon didn’t help you, but the best way it helped me is that going there just gives you an opportunity to get all the bad comedy writing out of your system early. The connections certainly do help, but it’s more that it’s a laboratory that I was lucky enough to have, to try out stuff and learn what was really bad.”

Despite Dan’s passion for writing at Harvard, upon graduating he was initially going to pursue a legal career. Dan recalls a particularly illuminating turning point shortly after graduating. He had been accepted into the University of Chicago Law School and was mostly packed and ready to go, when he had the almost surreal, slow-motion realization that law school was not his future.

Instead, Dan accepted his first job as a junior editor for the National Lampoon. His initial plan was to settle into a long-term career writing for a magazine, not television or Hollywood. However, his trajectory at the National Lampoon was not as he intended. Dan recollects, “I thought, my dad was on the Reader’s Digest 35 years, so I’ll probably be here 35 years. I was there nine months, and they canned most of us.”

After the National Lampoon, Dan did a brief stint at Cracked magazine, but he soon realized the print world was dying and began his foray into television by writing for what he describes as “crappy little cable shows, mostly for MTV.” Not long after, Dan landed a position working for the famed Tonight Show with Jay Leno.

Dan remembers, “I heard they were looking, just through the grapevine, and I found out who to get in touch with and I pestered them and finally they met with me.” But it was a bit more complex than that. Prior to landing the job at Leno, Dan was nearly hired at both Late Show with David Letterman and Late Night with Conan O’Brien. For one reason or another, neither of those two panned out, but the head writer for Conan had been fond of him and recommended him to the Leno show. Dan states, “Because of the recommendation from the very generous head writer of Conan, I got relocated to LA.” Of his experience at the Tonight Show, Dan says, “I was there for a year and a half and [Leno] was a really, really nice guy. He was really generous and good to work for.”

After Leno, Dan worked for about a year on the show Married With Children until a change in the show’s leadership left him unemployed for nearly a year. This was the most difficult period of his writing career, a time during which Dan considered giving it all up. Dan recalls, “I sent in an application to an armored car company.”

It was during this period that he set his sights on Seinfeld. “I reconnected with some people on Seinfeld that I’d known in college, and badgered them, and was given the opportunity to submit stuff.” Given that opportunity, he sent them pages of ideas every Friday for “months and months.” His trademark persistence paid off. Eventually Jerry Seinfeld came across some of those pages and liked his work. Dan was hired as a freelance writer for season eight, and was staffed on Seinfeld full time by season nine.

Fans of Seinfeld have Dan to thank for the introduction of Festivus, a holiday invented by his father that Dan wrote into the famous episode, “The Strike.” It might be surprising to learn, however, that his inclusion of Festivus was not done without some prodding by his fellow staff writers. It’s safe to say Dan’s relation to the holiday is similar to that of character George Costanza in the episode. His personal experience was “mostly bizarre and terrifying,” and although he is not averse to the holiday in theory, he does not celebrate it and the overall fascination with it still “boggles my mind.”

After Seinfeld, Dan worked for six years on The Drew Carey Show, six years on The League, and is currently writing for and co-executive producing the HBO hit Silicon Valley. Dan describes working on Silicon Valley as a good challenge and incredibly rewarding, with a remarkable cast and crew.

Reflecting on his writing experience as a whole Dan notes, “It’s rare to work on a popular show with fun, good people also. There are three pairs of variables to each show experience: good or bad in terms of quality, popular and unpopular shows, and with fun or horrible people. I had experienced every possible combination until Silicon Valley, when, for the first time since Seinfeld, all was positive.”

Having recently wrapped season 3 of Silicon Valley, Dan is enjoying the temporary hiatus between seasons. In the interim, he is working on a project with his brother, Mark, who is also a successful Hollywood screenwriter. Their collaboration is one year in the making and somewhat of a passion project, as they have never actually worked together.

As for his advice to aspiring writers, he says, “Do something else, it is very difficult and unstable”—but as most aspiring writers will disregard that standard disclaimer, he insists that they be prepared for the long game and disciplined about actually writing, every day when possible. He also recommends working on multiple projects simultaneously to “hedge your bets,” and not to show your work until it is the best it can be, as executives will not see your work for what it could be, but for what it currently is. He also emphasizes “no typos” and “don’t be a Hollywood cliché and buy a boat the next day, be smart with your money.”

We conclude our meeting and part ways, and he returns to his wife, adorable six-year-old son, and fifteen-year-old dog Duppy at his home in the Los Feliz hills.

To see some of Dan’s recent work, watch the season three premiere of Silicon Valley, and for any aspiring writers out there, remember—no typos.