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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.[2] 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,[2] at No. 3. In addition, the album earned a gold certification from the Recording Industry Association of America (RIAA) for shipping 500,000 copies.[1] 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.[3] American Child[edit] American Child was Vassar's second album, once again co-produced with Gallimore. It was released in 2002, the same year in which he married Julie Wood, with whom he co-wrote "That's When I Love You". The album's title track served as its lead-off single, reaching a peak of No. 5 on the country charts, and the album itself peaked at No. 4 on the Top Country Albums charts. In mid-2002, he also co-wrote and performed a charity single called "Words Are Your Wheels" to promote literacy. Released exclusively through Walmart stores, this song featured guest vocals from Kenny Chesney, Brooks & Dunn, Martina McBride, and Sara Evans.[4] While "American Child" was climbing the charts, Arista tested another song written by Vassar, "This Is God". The song was so well received by test audiences that American Child was re-released in early 2003. The re-issue featured "This Is God" along with a cover of Huey Lewis and the News's "Workin' for a Livin'", with Dann Huff producing both recordings. "This Is God" was issued as the album's second single, becoming a Top 20 country hit. After it, came "Ultimate Love", which peaked at No. 41. Shaken Not Stirred and Greatest Hits[edit] In 2004, Vassar released his third studio album, Shaken Not Stirred. The album produced Vassar's second No. 1 as a singer in the song "In a Real Love". Also released from this album were the No. 17 "I'll Take That as a Yes (The Hot Tub Song)" and the No. 22 "Good Ole Days". Unlike with his first two albums, Vassar recorded Shaken Not Stirred with his road band. Vassar produced the album with Nick Brophy and Frank Rogers. Vassar's first greatest hits compilation, Greatest Hits, Vol. 1, was issued in 2006. This album comprised the biggest hits from his studio albums to that point, as well as his renditions of "Bye, Bye", "I'm Alright", "My Next Thirty Years", and "Little Red Rodeo". The album also included three new songs. Two were released as singles, starting with the No. 2 "Last Day of My Life", which Vassar was inspired to write after attending the funeral of his