In 2000, Baker formed Timothy's Weekend, a pop-punk band, with future Annuals members, Kenny Florence (lead vocals, guitar) and Mike Robinson (bass).

25 entry in Pitchfork’s "Infinite Mixtape" series with their song "Brother" and received extensive coverage in such publications as Rolling Stone, Spin, Paste, Stereogum, Filter, NME, BrooklynVegan and AbsolutePunk, and others.

[5] A far more polished product than its predecessor, the album was co-produced by Grammy award-winning producer Jacquire King (Tom Waits, Modest Mouse, Dawes) and features an original Bob Ross painting as the cover art.

Written, recorded and produced entirely by Baker,[6] the 5-song EP featured four original songs and one cover (Johnny Cash's "Flesh and Blood”), and showcased yet another evolution in the band's sound.

New band members Tim Casey (drums), Britt Rand (keys), Jordan Robins (guitar), Eric Notarnicola (bass) came on board to form the new lineup.

[14] In a 2009 interview with LAist, Baker cited Mike Patton (Faith No More, Mr. Bungle), Brian Wilson and the Beach Boys, Hank Williams Sr., Johnny Cash, Radiohead, Bjork, and Secret Chiefs 3 among his major influences.

[15] Annuals made their national television debut on Late Night with Conan O'Brien performing the song "Carry Around", and came back in October 2008 for a second show, playing "Confessor", the opening track from their album, Such Fun.