Bolton's breakthrough came in 1983 with the release of , a single that reached the top 10 on the Billboard Hot 100 chart. This success was followed by his debut album on Columbia Records, "New York Sessions" (1983), which featured the hit single "How Am I Supposed to Live Without You" . The album was a commercial success, and Bolton's soulful voice and songwriting skills earned him critical acclaim.

Bolton's subsequent albums, (1991) and "Timeless: The Classics" (1992), continued to showcase his vocal prowess and songwriting skills. "Timeless" was a critically acclaimed album that featured Bolton's interpretations of classic standards, including "The Way You Look Tonight" and "You Don't Bring Me Flowers" .

Throughout the late 1980s, Bolton continued to release hit albums and singles, including (1987) and "I'll Be Home for Christmas" (1989). His music often featured a mix of pop, rock, and R&B elements, which appealed to a wide audience.