Jenny and Johnny - Im Having Fun Now (2010)

Rilo Kiley

In 1998, Lewis and friends Pierre De Reeder, Dave Rock and then-boyfriend Blake Sennett formed the band Rilo Kiley. (Rock was eventually replaced by Jason Boesel.) In an interview with NPR's All Songs Considered, Lewis remarked that she wanted to name the group Love's Way (after her parents' lounge act in Las Vegas), but Sennett "didn't go for it."[9]

Beginning with a country sound, Rilo Kiley gravitated toward a downbeat indie rock sound, gaining the attention of Warner Bros., who signed the band for the release (via its own imprint, Brute/Beaute Records) of their 2004 album More Adventurous, which gained the band some success. Critics such as Pitchfork attributed this to the "wise" decision to emphasize Lewis's voice and presence more so than in previous albums.[10] The song "Portions for Foxes" was a hit. The band opened for Coldplay on its U.S. tour in 2005. Rilo Kiley's 2007 album Under the Blacklight was released directly by Warner Bros.

It was announced on July 14, 2011 that Rilo Kiley had officially split up, with speculation that the loss of Jason Boesel to Bright Eyes and Jenny Lewis' other projects meant the band just fell apart.
Solo career
Lewis in 2006

In 2004, Conor Oberst invited Lewis to record a solo record for record label Team Love. Described by Lewis as "a kind of soul record"[citation needed], Rabbit Fur Coat (released January 24, 2006) features contributions from Oberst, M. Ward, and Maroon 5 guitarist James Valentine. Ben Gibbard of Death Cab for Cutie guests on a cover of The Traveling Wilburys' "Handle With Care." The Watson Twins provide accompaniment on the album, billed as Jenny Lewis with the Watson Twins. Lewis toured with the Watson Twins in support of the album three times in 2006 and appeared with her band on the Late Show with David Letterman, The Late Late Show with Craig Ferguson, Late Night with Conan O'Brien and Later with Jools Holland. They also appeared on a Washington, D.C.-based children's music program called Pancake Mountain, performing the song "Fernando". The album received positive reviews, with Entertainment Weekly writing, "Consider Lewis the Emmylou Harris of the Silverlake set"[11] and Rolling Stone commenting that "her girlishly seductive vocals are more versatile than ever".[12] The Onion AV Club, Spin, and NPR music critic Meredith Ochs named it among the best albums of the year.[13][14][15]

In 2008, Lewis released a second solo album, this time without the Watson Twins, titled Acid Tongue.
Jenny and Johnny

In 2010, Lewis released the song "Scissor Runner" with her boyfriend Johnathan Rice under the moniker Jenny and Johnny. The song was made available for free download from the duo's official website, and is taken from their first studio album I'm Having Fun Now.[16]
Other musical projects
Lewis performing in 2007

In 2002, Lewis was asked to contribute vocals for The Postal Service. Lewis performed in the video for the hit "We Will Become Silhouettes", and toured with the band in 2003. Lewis contributed vocals to several tracks on the 2004 Cursive album The Ugly Organ.

In 2005, Lewis contributed to the UNICEF benefit song "Do They Know It's Hallowe'en?", along with Sennett and Jimmy Tamborello.

In 2006, Lewis made a cameo in Episode 25, Season 1 of Bob Dylan's Theme Time Radio Hour, and six of her songs (three with the Watson Twins and three with Rilo Kiley) were featured in various episodes of the show.

In 2007, Lewis contributed vocals to various songs on Johnathan Rice's album Further North, and she appeared in the music video for "We're All Stuck Out In The Desert (And We're Gonna Die)". She provided vocals for a track on Dntel's Dumb Luck LP.

In 2008, Lewis contributed backing vocals to several songs on the Elvis Costello and the Imposters album Momofuku.

In 2008, Lewis voiced the role of the Assistant Director for Walt Disney Pictures Bolt and provided the song "Barking at the Moon." [17]

In March and April 2009, Lewis traveled to Australia for the first time, as an act for the V Festival, as well as a supporting act for Snow Patrol and performing one solo Sydney show.

On April 18, 2009, Lewis performed at the Coachella Valley Music and Arts Festival in Indio, California.

On May 5, 2009, Lewis performed on The Late Late Show with Craig Ferguson.[18]

Lewis makes an appearance on the track "Hard Enough", taken from the 2010 album Flamingo by fellow Las Vegas resident Brandon Flowers.