Before Barack Obama ran for re-election, Lovett moved to California to become a Screenwriter. There Lovett collaborated with Josh Gad and Jason Winer on 1600 Penn, of which Lovett was a co-creator, executive Producer, and Writer from 2012 until 2013. Lovett then worked as a Writer, Producer and advisor on season three of HBO's The Newsroom.
In 2004, Lovett volunteered for John Kerry's presidential campaign. He was asked to write a statement for the candidate, and his work led to an offer of a writing internship. He then briefly worked in Jon Corzine's Senate office.
He was hired in 2005 to assist Sarah Hurwitz as a speechwriter for then-Senator Hillary Clinton, and he continued to write speeches for her through her 2008 presidential campaign.
When Clinton lost the 2008 Democratic primary contest, Lovett won an anonymous contest to write speeches for President Barack Obama in the White House. Lovett wrote speeches in the Obama administration for three years, working closely with Jon Favreau and David Axelrod. Prominent speeches that he wrote include policy speeches on financial reform and don't ask, don't tell, as well as remarks at the White House Correspondents' Dinner.
Shortly after the November 2016 election, Lovett, Favreau and Vietor founded their own company, Crooked Media, and launched a new podcast, Pod Save America. In March 2017, Lovett began hosting Lovett or Leave It, a panel show podcast from Crooked Media, recorded in front of a live audience in Los Angeles. Lovett and Crooked Media have embarked on national and international tours featuring live versions of Pod Save America and Lovett or Leave It.
