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Fronted by former child actors Jenny Lewis (Troop Beverly Hills, The Wizard) and Blake Sennett (Salute Your Shorts, Boy Meets World), the band signed with independent label Barsuk Records for its first full-length album, Take-Offs and Landings, in 2001. The band later signed with Omaha's Saddle Creek Records and released The Execution of All Things in 2002. In 2004, it released More Adventurous on its own imprint, Brute/Beaute Records, which was distributed by major label Warner Bros.. The band later signed directly with Warner Bros.

2004 saw a great increase in recognition for the band, as Sennett and Boesel released an album with their band The Elected and Lewis sang backup on Ben Gibbard's indie electronic Death Cab for Cutie side project The Postal Service. Lewis toured with The Postal Service before heading out on two tours in support of Rilo Kiley's More Adventurous in the summer and fall of 2004. The album spent late 2004 high on Billboard's Heatseekers Chart, and was promoted with appearances on the Late Night with Conan O'Brien and Jimmy Kimmel Live. The band opened for Bright Eyes on the international leg of Conor Oberst's tour for 2005's I'm Wide Awake, It's Morning and was the opening act for the North American dates of Coldplay's Twisted Logic Tour in Fall 2005. "I Never" and "Ripchord" (from More Adventurous) have been featured in several feature films, including Must Love Dogs, Conversations with Other Women, and John Tucker Must Die.

The band's songs have frequently been used on television programs, such as The O.C. and Dawson's Creek. The apparent first use of Rilo Kiley music on a television show was also the last time that Blake Sennett and Jenny Lewis acted on television. In 2000, they played fictionalized versions of themselves (and the band performed "The Frug") on ABC's short-lived drama Once & Again. Both "The Frug" and "85" were used during a third season episode of Dawson's Creek (#46, "Barefoot At Capefest"). Commenting on this, Lewis said, "We felt honored and grateful to have our music on a show with the integrity and credibility that Dawson's Creek has so rightly earned. We feel proud also that they chose to play our songs during such poignant points in the episode."[1] "Pictures of Success" was used in episode #114 of Buffy The Vampire Slayer, entitled "Older and Far Away". In 2005, "Portions For Foxes" was used in the pilot of Grey's Anatomy and "With Arms Outstretched" was used in the pilot of Weeds. For a second-season episode of Weeds, Lewis sang the theme song ("Little Boxes") with Johnathan Rice who was touring with the band. "Silver Lining" was featured in the pilot of "Women's Murder Club". The song "Breakin' Up" was featured in a fourth season episode of Grey's Anatomy. "The Moneymaker" was used on an episode of "Nip/Tuck" that aired on December 11, 2007 and on an episode of Samantha Who? that aired on April 16, 2009. "The Good That Won't Come Out Of Us" was featured quietly in the background of the Season 4 Episode 4 episode of "Heroes (TV series)" "Hysterical Blindness" on 10/12/2009.

The group is also known for its charitable contributions, particularly to the Elliott Smith Memorial Fund, in honor of the late singer and friend of the band. Sennett and Lewis participated in a memorial concert for the singer shortly after his death in 2003. Sennett and Lewis also contributed to the 2005 UNICEF benefit song, "Do They Know It's Hallowe'en?".

The band's fourth album Under the Blacklight was released August 20, 2007 in the United Kingdom[2] and the following day in the United States.[3] Its first single is "The Moneymaker". For the video, the band cast "real-life porn stars", who Lewis says were told they were auditioning for "soft core porn".[4] The second single is "Silver Lining".

On September 6, 2007, the band began a North American tour in support of Under the Blacklight. On this tour, it was joined by Orenda Fink (of Azure Ray) and Kristin Gundred (of Grand Ole Party).