In the fall of 1996 Lars Bygdén convinced some of his friends to start a band. The $1000 Playboys played their first gig that December at Pipeline (in Sundsvall) and totally stunned the audience. And this was just the beginning. Peter Svensson of the Cardigans saw the band perform and he realized that this was a band aiming for the stars. Svensson financed an album recording at Tambourine Studios in the fall 1997. The road to fame seemed paved and ready. But after 1½ year of fruitless negotiation with several labels they still had no record deal.

In the winter of 1999, the band signed with independent record label Massproduktion. A new recording session was planned. Meanwhile, national Swedish radio P3 broadcast the Playboys live during a PopStad event and this was released as a track on the promotional CD "The Rope". The $1000 Playboys were now in rotation on national radio despite the fact that they still hadn't released an album!

In May the recordings started, now with Linus Larsson as producer. A wide variety of guests are featured on the album and several of the tracks were captured live in the studio…only three tracks from the Tambourine recordings made it to the self titled debut album (released 25 October 1999).

The first single "Preacher" was play-listed for 8 weeks by the National Radio P3. Spring 2000 meant a new video, a new single and more gigs all over Sweden. The fall tour under the name "Järnvägar!" was filmed by National TV and resulted in a documentary that was broadcast late 2000.