[1] The band soon signed to Drive Thru Records/MCA and flew to Los Angeles to record with Jon Naclerio at Hans Zimmer's Media Ventures Studios.

Released on April 19, 2005, Twilight Tales From The Prairies on the Sun features appearances by famed mandolinist David Grisman, as well as pedal steel guitarist Gene Parsons (The Flying Burrito Brothers/The Byrds).

In support of the album, Steel Train toured with Ace Enders and A Million Different People, Socratic, Kevin Devine, The Starting Line, Paper Rival, Bayside, and Forgive Durden, among other bands.

[16] Following the Late Night with Conan O'Brien performance and a tour with The Hush Sound, the band headed back into the studio, this time to record their third full-length album with producer Steve McDonald (Be Your Own Pet, Fun).

Once again the band hit the road, touring with Tegan and Sara, Ben Folds, and Fun, as well as playing 2010's Coachella Music Festival and making their 2nd appearance on National TV on the Late Show with David Letterman.

1", includes appearances by Tegan and Sara, Scarlett Johansson, Deradoorian of Dirty Projectors, Amanda Palmer, Anna Waronker of That Dog, Alia Shawkat, Charlotte Caffey of The Go Go's, Rachael Cantu, Rachel Antonoff, Holly Miranda, and Greta Salpeter of The Hush Sound and Gold Motel.

[24] In August 2010, Steel Train was a guest on Anything Anything with Rich Russo where they performed three songs: "Bullet", "I Feel Weird", and a cover of Tegan and Sara's "Call it Off".

The band, along with actor Jim Parsons (The Big Bang Theory) performed one chord off their new record, Steel Train, in a short version of the show.