The band's members are Kay Hanley, Greg McKenna, Michael Eisenstein, Stacy Jones, Scott Riebling, and later, Tom Polce and Joe Klompus.

The band was initially called Rebecca Lulu,[4][5] with Tad Bouve on guitar and Ted Garland on drums with several musicians filling in on bass.

The band released a 45 single of "Here & Now" with Rimshak featuring Abe Laboriel on drums with Brian Karp on bass.

The band's definitive lineup of Hanley, McKenna, Michael Eisenstein on guitar, Stacy Jones on drums, and Scott Riebling on bass, was established in 1994.

The band also recorded a cover of The Cars song "Dangerous Type" for the major motion picture The Craft.

Letters to Cleo appeared in the 1999 film 10 Things I Hate About You as a favorite band of the character portrayed by Julia Stiles.

[12] The band played its final show on May 4, 2000, a benefit for their friend and longtime local supporter, Mikey D.[13] They announced their disbandment the following month.

Kay Hanley provided the singing voice for Rachael Leigh Cook's character in the 2001 film Josie and the Pussycats.

In December 2007, an impromptu reunion occurred when four of the original band members appeared at a benefit for longtime supporter Jeanne Connolly, at TT the Bear's Place in Cambridge, Massachusetts.

In the Parks and Recreation Season 4 episode entitled "The Comeback Kid", the character Ben Wyatt is seen wearing a Letters to Cleo shirt[15] (show star Amy Poehler attended Boston College during the band's early years).

[19][20] The band's Facebook and Twitter feeds have been active with status updates, pictures and videos of ongoing recording.

[25] In 2023, band members Kay Hanley and Tom Polce wrote ten original songs for "Subspace Rhapsody," the musical-themed ninth episode of the second season of Star Trek: Strange New Worlds.

Most notable is Kay Hanley's career, which produced the albums Cherry Marmalade in 2002, The Babydoll EP in 2004, and Weaponize in 2008.

Hanley and Eisenstein married in the late '90s and have two children, Zoe Mabel and Henry Aaron (named for legendary baseball Hall Of Famer).

Drummer Stacy Jones went on to form American Hi-Fi with fellow Boston musicians Drew Parsons, Jamie Arentzen and Brian Nolan.

Previous gigs also include playing drums for Matchbox Twenty, Madonna, Dia Frampton, Veruca Salt, Avril Lavigne, Ariana Grande, Joan Jett, Against Me!, The Jonas Brothers, The Flaming Lips, Lily Allen, Billy Ray Cyrus, Sheryl Crow, Cobra Starship, Aimee Mann, The Cab, Hey Monday, Butch Walker, and more.

On the television show Parks and Recreation, Ben Wyatt (Adam Scott) wears a Letters to Cleo shirt on multiple occasions while he is between jobs.