He became a cultural icon because of his work in television, but Regis Philbin originally thought his singing would bring him stardom. The native New Yorker grew up listening to radio station WNEW, and Bing Crosby's and later Dean Martin's radio programs. The first record he bought was Crosby's "Swinging on a Star," the second was Martin's "One Foot in Heaven," and Philbin spoke numerous times in interviews about how large both men were in influencing his singing style. 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 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 standards-filled debut, It's Time for Regis!, in 1968. Philbin went on to host successful daytime talk shows and game shows, but it was his 1985 job with Kathie Lee Gifford that put his career over the top. Live with Regis & Kathie Lee took daytime television by storm, and when Gifford left and was replaced by Kelly Ripa in 2001, the show retained its audience without missing a beat. In 1999, Philbin became the host of Who Wants to Be a Millionaire, one of the most successful prime-time game shows ever.

Philbin 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." A year later he returned with The Regis Philbin Christmas Album, which included appearances by Steve Tyrell and Donald Trump. Just You. Just Me., an album of duets with his wife, Joy Senese, was released in 2009 by Big Dot Records. Regis Philbin died on July 24, 2020; he was 88 years old. ~ David Jeffries