In late 1999, Vassar was signed to his first recording contract, with the Arista Nashville label.
His debut single, "Carlene", was issued that year, and by mid-2000 the song had gone on to peak at No.
 5 on the Billboard country charts.
It featured a backing vocal from Collin Raye.

The song was the lead-off single to Vassar's self-titled debut album, which he co-produced with Byron Gallimore. "
Carlene" was followed by "Just Another Day in Paradise", his first No.
 1 hit as a singer.
Shortly after that song peaked, Tim McGraw topped the charts with "My Next Thirty Years", which Vassar co-wrote.
 Overall, Phil Vassar produced three more singles: the No.
 16 "Rose Bouquet", "Six-Pack Summer" at No.
 9, and finally "That's When I Love You", with a backing vocal from Jo Dee Messina, at No.
 3.
In addition, the album earned a gold certification from the Recording Industry Association of America (RIAA) for shipping 500,000 copies.
Its success led to tours with Kenny Chesney.

Vassar also co-wrote the tracks "God Bless This Town" and "Live It Up" on Marshall Dyllon's late 2000 debut album Enjoy the Ride, in addition to co-producing them with Robert Byrne.
The latter was released as a single.
In late 1999, Vassar was signed to his first recording contract, with the Arista Nashville label. His debut single, "Carlene", was issued that year, and by mid-2000 the song had gone on to peak at No. 5 on the Billboard country charts. It featured a backing vocal from Collin Raye.
The song was the lead-off single to Vassar's self-titled debut album, which he co-produced with Byron Gallimore. "Carlene" was followed by "Just Another Day in Paradise", his first No. 1 hit as a singer. Shortly after that song peaked, Tim McGraw topped the charts with "My Next Thirty Years", which Vassar co-wrote.  Overall, Phil Vassar produced three more singles: the No. 16 "Rose Bouquet", "Six-Pack Summer" at No. 9, and finally "That's When I Love You", with a backing vocal from Jo Dee Messina, at No. 3. In addition, the album earned a gold certification from the Recording Industry Association of America (RIAA) for shipping 500,000 copies. Its success led to tours with Kenny Chesney.
Vassar also co-wrote the tracks "God Bless This Town" and "Live It Up" on Marshall Dyllon's late 2000 debut album Enjoy the Ride, in addition to co-producing them with Robert Byrne. The latter was released as a single.
Phil Vassar