Nagler met and befriended fellow former child actor Blake Sennett in the mid-1990s. Soon after, Sennet and Jenny Lewis formed the band Rilo Kiley in 1998, and Nagler also began writing songs and singing. In 2004, Nagler performed her songs before a live audience (with help from friend Tod Adrian Wisenbaker) as the opening act for the Elected, Sennett's side project from Rilo Kiley. Nagler credits Sennett and Lewis for giving her the support to record and perform her own songs.[citation needed]
In 2005, Nagler and Wisenbaker named their group Whispertown 2000 and asked Vanesa Corbala and Colt Maloney to join. During the fall 2006 tour, Casey Wisenbaker (Tod's brother) also joined the band. Their debut album, Livin' in a Dream, was released in 2006. It was produced by Sennett and Jimmy Tamborello (of Dntel and the Postal Service). Additional performers included Sennett, Jenny Lewis and Johnathan Rice. Maloney parted ways with the band in 2007.
On October 21, 2008, the band released their second full-length album, Swim, on Acony Records. Along with this new release, the official name of the band changed to the Whispertown 2000 (with definite article "the" included). Additional performers included Lewis, Gillian Welch and David Rawlings. Nagler co-wrote "Sweet Tooth" from Rawlings' 2009 album A Friend of a Friend.
On March 20, 2012, Nagler released the EP Parallel under the name Whispertown. Parallel was her second release on Acony. The EP was recorded and mixed by Andy LeMaster (of Bright Eyes), co-produced by Jake Bellows (of Neva Dinova) and executive produced by Rawlings.[4]NPR premiered the video for the title track on July 3, 2013, calling it "luscious and expansive".[5]Paste gave Parallel a 7.1 out of 10, calling it "resoundingly solid ... keeping a balance between two divergent aesthetics (singer-songwriter fare and classic country heft)."[6] In August, Nagler was featured in Rolling Stone's profile on Laurel Canyon's revival at the home of Jonathan Wilson, and how "the former L.A. home base of Joni Mitchell and Jackson Browne is now a hub to a new wave of hippie rockers."[7]
In 2014, Kim Deal and Nagler released a 7-inch single, "The Root"/"Range on Castle".[9]Pitchfork premiered the video for "The Root" on March 21, 2014.[10] The lyric video for "Range on Castle" was premiered by Bob Boilen on NPR Music on July 10, 2014.[11]
Whispertown released I'm a Man on September 1, 2017, on Graveface Records.[12] The title track premiered on Impose on July 17, 2017, and was KCRW's "Top Tune" on August 17, 2017.[13] In October, Whispertown opened for M. Ward on a string of west coast dates.[14] Nagler appeared in the video for the title track from Kevin Morby's 2017 album, City Music.[15]