He first came into the American home on a national level by playing sidekick to Joey Bishop on the Rat Packer’s late-night talk show, which aired from 1967 to 1969. It was on that show that Philbin lived one of his dreams, performing “Pennies from Heaven” as a duet with Bing Crosby. Someone from the Mercury label caught the duet and was impressed enough to offer Philbin a chance to record an album. The label issued his standard-filled debut, It’s Time for Regis!, in 1968. Philbin went on to host daytime talk shows and game shows that were successful. In 1999, Philbin became the host of Who Wants to be a Millionaire, one of the most successful prime-time game shows ever. Philbin, who had been making singing appearances in Atlantic City, Las Vegas, and Connecticut for most of the ’90s, occasionally broke into song on his daytime show, and had his debut reissued on CD in 1994, but there were no new releases for his — now huge — fan base. Philbin corrected this oversight in 2004 when he released When You’re Smiling on the Hollywood Records label. The CD included a new version of the song that meant so much to Philbin for all these years, “Pennies from Heaven.” Philbin is currently preparing a new, sports-related talk show. He continues to perform around the world.
