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Jon Lovett’s written for the president, but will that get him to Hollywood?

By Jason Horowitz,September 02, 2011

Jon Lovett is leaving his job at the White House to pursue screenwriting… (Marvin Joseph/WASHINGTON…)

A young and witty speechwriter for an eloquent but exhausted president escapes a struggling White House and stodgy capital city for Hollywood, where he beats the odds to find fame and fortune writing comedy for more bankable stars.

So might read the script treatment about the aspirations of Jon Lovett, an Obama speechwriter and the reigning champion of official Washington’s stand-up comedy circuit. In mid-September, Lovett, 29, plans to leave the administration to write for television out west.

“It’s always been a dream of mine to write comedy and be creative,” said Lovett, who insisted that West Wing woes had nothing to do with his timing. “I would like to be able to write in my own voice.”

The transition from speechwriter in a company town governed by cutthroat power dynamics to screenwriter in a company town governed by cutthroat power dynamics would seem seamless.

Except that it almost never happens.

Lovett is the latest Washington communications professional to try to translate his skills in campaign spin, prepared remarks and news releases into entertainment for the masses. His dream of branching out, or cashing in, with a screenplay or sitcom is one New York magazine writers and editors have long harbored. They’ve had so many stories optioned — if not actually made into movies — that formal relationships between New York news outlets, talent agencies and studios have become commonplace. The success rate of Washington writers is worse, perhaps because the town’s highest accolade is “insider,” or because a city populated by self-styled alphas isn’t exactly a breeding ground for comedic angst.

“It’s a town that really showcases a pretty limited number of skills,” said Reid Cherlin, a good friend of Lovett’s, who recently left a White House communications job to pursue a writing career in New York. “When you talk about being funny, or doing entertainment, what you are really talking about is stepping back and thinking critically and making connections.”

Hollywood has valued Washington power brokers more as executives than as creative forces. Chad Griffin, a former aide to President Bill Clinton, college roommate of White House communications director Dan Pfeiffer and former partner of Kristina Schake, Michelle Obama’s communications director, works in the intersection of Washington and Hollywood as a political strategist in Los Angeles. He said there is more of a track record of people from Hollywood going on to big things in politics — Ronald Reagan, Arnold Schwarzenegger, Al Franken — than the other way around.

Kal Penn explained that the dearth of creativity in Washington left him hungering for L.A., and the lack of intellectual life in L.A. left him longing for Washington. Penn left a successful acting career for a youth outreach position in the Obama White House, and last month returned to Hollywood, where he is developing a sitcom set at the United Nations and appearing in “How I Met Your Mother.”

“My view of D.C. and L.A. is that they’re almost the yin and yang,” said Penn, who described Lovett as a kindred creative spirit with whom he brainstormed short films last summer.

* * *

The thin list of notable Washington names who have worked in Hollywood includes congressional staffer turned “West Wing” writer turned cable host Lawrence O’Donnell and political consultant turned screenplay dabbler Mike Murphy. But the best current example is Eli Attie, a former Clinton White House and Al Gore speechwriter who became a “West Wing” scribe, then a successful writer and producer on the medical drama “House.” Attie, who has become immersed in West Coast ways, spoke reverently about the “craft” of television writing, of “emotional arcs” and “huge bombs.” He signed off by saying “ciao.”

Despite their shared sharkiness, the towns, Attie said, “are not really similar.” Washington, he said, is a place that rewards intelligence but not imagination, policy chops but not perspective, people who can frame arguments but not writers who think in “three dimensions.”

“In television, you have to really want to write,” said Attie, who added that a Washington ground rule dictates that speechwriters pretend never to have written any of their primary actor’s good stuff.

“And if you really want to write,” said the television writer, “why were you a speechwriter?”

For Lovett — who has interest from studios for a Washington-based political comedy and a “M*A*S*H” update — the answer lies in the apparently haphazard opportunities and chance connections that often shape a career.