The group recorded a number of creative albums and earned a small but loyal following. In 1997, the group signed to Steve Taylor's Squint Entertainment and released a self titled album that would catapult them into instant stardom. A short, quirky tune called "Kiss Me", that was nearly left off the album by the band, became the band's first number one single. The Grammy nominated song became the top airplay song in over 10 countries including Canada, the UK, Japan, Australia, and Israel and was also featured in a number of motion pictures (She's All That) and TV Shows (Dawson's Creek, Saturday Night Live, MTV's The Real World, The Young and The Restless, Days of Our Lives and others). The video for the song became VH1's #1 video for the entire month of May. In June of 1999, "Kiss Me" was featured during the BBC's worldwide broadcast of Prince Edward's wedding ceremonies, at the request of England's royal family. Over 200 million viewers tuned in.
In 2000, the band recorded a cover of The La's "There She Goes", which became their second hit single. Also that year, Sixpence contributed a song to Today Presents: the Best of Summer Concert Series CD, which raised money for the National Colorectal Cancer Research Alliance.
The band had a followup album ready to release, but unfortunately, Squint Entertainment started to fall apart - leaving the band in limbo for several years. Finally, Squint Entertainment was purchased by Word Records and that album, Divine Discontent, was released in October of 2002.
The band has what is almost a second career recording covers of other people's music for compilations and soundtrack albums. In addition to the previously mentioned "There She Goes", the band has recorded versions of "You're A Mean One, Mr. Grinch" (How the Grinch Stole Christmas), "I Just Wasn't Made for these Times" (The Beach Boys), "On The Run" (Electric Light Orchestra), "Boquet" (Steve Taylor), "I Need Love" (Sam Phillips), "Carry You" (Sam Phillips), "Don't Dream (It's Over)" (Crowded House), "Christmastime Is Here" (Vince Guaraldi, Peanuts), "Love Letters in the Sand" (Patsy Cline, Pat Boone and others), "Goodnight Children Everywhere" (Vera Lynn), "Road to Zion" (Petra) and "Dancing Queen" (ABBA).