Tomson grew up on a farm in the Imlaystown section of Upper Freehold Township, New Jersey, and later recorded parts of Vampire Weekend's first album there. His father is an engineer whose family is of Irish and Ukrainian heritage (he studied abroad in Ireland in college). His mother is an administrator whose family is of English and German heritage. He graduated from the Peddie School as a salutatorian and then from Columbia University where he studied economics and music. Tomson enjoys photography and is an avid soccer fan; his favorite club is Tottenham Hotspur. Tomson is also a huge fan of Phish, The Band, and the Grateful Dead. After living in the Greenpoint neighborhood of Brooklyn for several years, he moved to Los Angeles in 2019. In 2008 he was involved in a hit-and-run incident in London after the Shockwaves NME Awards. He was taken to hospital to be treated for neck injuries but was released with no notable injuries.
Prior to forming Vampire Weekend, Tomson played with Ezra Koenig in the "serious" rap group called L’Homme Run.
Tomson met the members of Vampire Weekend while attending Columbia University—he took music classes with Rostam Batmanglij and started the group in their senior year. The name of the group comes from the movie of the same name that Ezra Koenig and his friends made over a summer vacation. They self-produced their first album after graduation while concurrently working full-time jobs (Tomson worked as an archivist for a record label). Their next three albums – Contra (2010), Modern Vampires of the City (2013), and Father of the Bride (2019) – all reached number one on the US album charts.

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