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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.
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. 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" In 2008, Lewis released a second solo album, this time without the Watson Twins, titled Acid Tongue. The album took 5 years to complete and is a reflection on Rilo Kiley's break-up and the death of Lewis's father.
The music video for "Just One of the Guys" was released on July 15, 2014 through GQ and stars Lewis, Anne Hathaway, Kristen Stewart, Brie Larson, and Tennessee Thomas, former drummer of The Like (now disbanded).
In 2010, Lewis formed the duo Jenny and Johnny with her then-boyfriend, musician Johnathan Rice, and the pair released an album titled I'm Having Fun Now on Warner Bros. In 2015, Rice and Lewis wrote the song "Cold One" for the film Ricki and the Flash.
She was featured in the 1996 made-for-TV movie Talk to Me with Yasmine Bleeth, as well as the films Foxfire, Big Girls Don't Cry... She played the part of Evangeline "Eva" Saint Claire in the 1987 film version of Harriet Beecher Stowe's novel Uncle Tom's Cabin, and also appeared in 1988 made-for-TV film set in Vienna at the start of the Holocaust, A Friendship in Vienna.
She played Beverly D'Angelo's daughter in the 1996 made-for-TV film Sweet Temptation.
In the mid-1990s, Lewis semi-retired from acting to focus on her musical career, and formed Rilo Kiley in 1998 with fellow former child actor Blake Sennett.In 2005, Lewis contributed to the UNICEF benefit song "Do They Know It's Hallowe'en? 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.