Freelance Whales was founded during 2008, after connecting through Craigslist and friends of friends. The band's debut album, Weathervanes, was largely composed by frontman Judah Dadone, the lyrics based on a combination of childhood memories and dream journaling. Because they're from New York, the band's name derives from that freelance atmosphere that the city has. Judah Dadone, once said: 'Everybody in New York is a freelancer of something, and we used to be too when we played in the subways'. Multi-instrumentalist Chuck Criss was the brother of actor and singer Darren Criss.
The band began to gain traction in October 2009 as they honed their sound on subway platforms around New York City. Toward the latter part of 2009, they self-released Weathervanes, and on April 27, 2010 the album was re-released under the band's record labels, Frenchkiss and Mom + Pop. To promote their record, the band toured regularly from early 2010 thorough Spring 2011.
In September 2010, Twitter selected Freelance Whales' music as the background for a video introducing a major rework of the service's user experience. The same song, entitled "Generator ^ First Floor", was also used by the NBC show Chuck in its 4th season premiere episode ("Chuck vs. the Anniversary"), which premiered September 20, 2010, as well as by Chevrolet in advertisements for the 2011 Chevy Volt. On October 12, 2010, the song "Broken Horse" appeared in an episode of One Tree Hill ("Nobody Taught Us to Quit"). Their song "The Great Estates" was also featured in an episode of the USA show Covert Affairs Season 1. Their song "Generator ^ Second Floor" was used on season 5, episode 1 of the British show Skins while "Location" was featured in episode 4. Their song "Starring" was used in season 2 My Life as Liz on MTV. "Starring" was also featured in an episode of Grey's Anatomy in Season 7. A 2011 Starbucks commercial also used "Generator ^ First Floor" as background music, as did the David Cornfield Melanoma Fund for their "Dear 16-year-old Me" melanoma awareness campaign. Their song "Hannah" was also used in the Australian television show Offspring. Their song "Location" from the Weathervanes album was featured in LOL, starring Miley Cyrus and Demi Moore.

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