Drake played various venues in his native Pennsylvania for several years before moving to Nashville, Tennessee, co-writing a 1996 single for Joe Diffie.
That year, he released three singles from his self-titled debut album, including "One Last Time", his first Top 40 entry on the Hot Country Songs chart.
In 2007, he signed to the independent Big Machine Records label, charting with the single "Say Yes", co-written by Brett James, Don Schlitz and Josh Turner.
At the same time, he pursued his career in country music, eventually fronting a band called Silverado in addition to performing solo.
[5] Other artists who recorded Drake's songs included Janie Fricke, Ricochet (the single "Can't Stop Thinkin' About That"[6]), The Oak Ridge Boys and Mark Chesnutt.
After the release of his album, Drake went on to become an opening act for Kenny Chesney and Brooks & Dunn, as well as performing on the Grand Ole Opry.
His first single for the label, "Say Yes" (co-written by MCA Nashville artist Josh Turner along with Brett James and Don Schlitz), became his second Top 40 country hit, peaking at 36.
The song, a tribute to the Pittsburgh Steelers, used the melody of Mark Chesnutt's 2004 hit "The Lord Loves the Drinkin' Man".