After graduating from Williams College with a degree in math (and a published thesis titled “Rotating Linkages in a Normed Plane”), Lovett hit the amateur comedy clubs in New York. A chance call from a college connection got him on the 2004 Kerry campaign, which led to a stint in then-New Jersey Sen. Jon S. Corzine’s D.C. office. In 2005, he received an e-mail from Hillary Rodham Clinton’s Senate communications director asking, “Are you funny?” Clinton needed a speechwriter for a roast of Barbara Walters, and Lovett’s bits won him a spot. He took on a discreet role with the Clinton campaign, helping out chief speechwriter Sarah Hurwitz, whom he joined in the Obama White House.
He wrote many of Obama’s speeches about financial reform and his “don’t ask, don’t tell” remarks. Colleagues, who insist that Lovett is truly hilarious and not just funny by D.C. standards, said he seeded laugh lines into Rahm Emanuel’s commencement speeches and wrote jokes for Obama’s White House Correspondents’ dinner remarks, for which “Lovett went into comedy overdrive,” according to his former boss David Axelrod.