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Secretly Canadian was founded in 1996 by Chris and Ben Swanson, Eric Weddle, and Jonathan Cargill while they attended Indiana University.[4][5][6] Before Secretly Canadian was founded, Chris Swanson and Eric Weddle met in 1995 in Indiana University's campus radio station, WIUX.[7][8] Then Chris met Jonathan Cargill through a job at the Collins Living-Learning Center cafeteria on campus.[9] Soon after, Chris' younger brother Ben Swanson moved to Bloomington to earn his undergraduate degree[10] from the Jacobs School of Music in musicology.[11][12]
In 1996, Secretly Canadian was founded.[13][14] The label's first official release was a re-issue of an album by June Panic from Grand Forks, North Dakota; the Glory Hole CD.[15] The second release in 1997 was Jason Molina's, under the Songs: Ohia moniker, often referred to as "The Black Album".[16] After the Swanson brothers tracked down Molina's email address and drove hours to Molina's in-store gig at Adult Crash in New York.[17][18] After signing Molina, the record label became more popular in the indie music scene.[19] Secretly Canadian then signed Marmoset and Swearing At Motorists.[20] Weddle soon left to form label Family Vineyard – and later followed by Cargill as well.[21] After that, Chris Swanson and Darius Van Arman became friends in 1999 and Secretly Canadian joined forces with Van Arman's Jagjaguwar.[22][23]
In 2007, the addition of Dead Oceans to Secretly Canadian and Jagjaguwar's partnership led to the formation of Secretly Group.[35] In 2015, Secretly Group began a partnership with The Numero Group as well.[36][37]
In 2018, Secretly Canadian was listed as #8 on Paste Magazine's top 10 record labels of 2018. Jagjaguwar was listed as #4 and Dead Oceans was listed as #7.[38]