With an adolescent Ween-like absurdist sense of humor that sometimes borders on creepy, Greenskeepers top bass-heavy beats with inside jokes, succeeding in taking a satirical home-recording project from the bedroom to the dancefloor before they were old enough to legally drink at a club. James Curd and Nick Maurer took the name Greenskeepers from the fact that they both paid the bills by working as golf course caddies. In their spare time they kept themselves occupied skateboarding the streets of Chicago, and Maurer performed as a singer/guitarist for various punk bands while Curd DJed the local scene. In 1998, the two paired up and wrote the amusing and danceable song "Should I Sing Like This." It became a minor club anthem and a set staple for DJ Derrick Carter, who released the song on Classic Recordings later that year. Several high-profile reviews about the band in the press caught the attention of multi-instrumentalist Mark Share, who sat in with Curd to help produce and put the final touches on their first full-length album, Present the Ziggy Franklin Radio Show!, in 2001.
After a break, in 2004 Share, Curd, and Maurer recruited bass player Coban Rudish to work on the second album, Pleetch (a combination of the words "please" and "bitch"). This mixed Roger and Zapp-motivated electro-funk, Alan Parsons Project-style slow jams, and house beats with absurd homages to Buffalo Bill from The Silence of the Lambs and Tattoo from Fantasy Island. Soon after, San Francisco indie Om Records licensed the songs "Lotion," "Man in the House," and "Go" to the ABC series Grey's Anatomy. Greenskeepers merged their beats with media again by remixing the theme song from the Pixar/Disney blockbuster The Incredibles on The Incredibles Remix EP. After a two-year world tour, in late 2006 their third album, Polo Club, took shape with heavy inspiration from '80s post-punk (especially Gary Numan and Talking Heads), and again featured their usual combination of quirky house music and twisted comedy, supplemented by guitar hooks and their trademark idiosyncratic vocals.