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Robert Hunter Caldwell (August 15, 1951 – March 14, 2023) was an American singer, songwriter, and musician. He released several albums spanning R&B, Soul music, jazz, and adult contemporary, and was known for his soulful and versatile vocals. Caldwell released the hit single and his signature song "What You Won't Do for Love" from his double platinum debut self-titled album in 1978.
After several R&B and smooth jazz albums, Caldwell turned to singing standards from the Great American Songbook. He wrote many songs for other artists, including the Billboard Hot 100 No. 1 single "The Next Time I Fall" for Amy Grant and Peter Cetera. Caldwell's musical catalog is perhaps best known today for its later sampling by several prolific hip hop and R&B artists.
Caldwell got his first career break as a rhythm guitarist for Little Richard in the early 1970s. Caldwell and his band eventually left Little Richard, and Caldwell went solo. By 1977, he had spent six years in Los Angeles playing in different bar bands and trying to get a record deal. Caldwell eventually signed with TK Records in Miami in 1978. After songs for his first album were recorded, executives told Caldwell they enjoyed the album, but thought it was lacking a hit. Caldwell returned to the studio for two days and wrote "What You Won't Do for Love". TK was mainly an R&B label popular among African American listeners. Executives at the label wanted to conceal the fact that Caldwell was white, so they kept his face off the album cover. When he toured with Natalie Cole to support the album, most of the audience was black and many were surprised that Caldwell was white.
"What You Won't Do for Love" on Bobby Caldwell reached the top ten on the Billboard magazine Hot 100 (No. 9) R&B (No. 6), and Adult Contemporary (No. 10) charts. The song has been covered, remade and sampled many times. Caldwell remade it in 1998. It was covered by Go West, Phyllis Hyman, Roy Ayers, Michael Bolton, Intro, Boyz II Men and Snoh Aalegra and was sampled by Tupac Shakur for his hit "Do for Love". It was covered by Elliott Yamin during the fifth season of American Idol in 2006. Caldwell's track "My Flame" is sampled for "Sky's the Limit" by The Notorious B.I.G. featuring R&B group 112.
Caldwell's debut album was followed by Cat in the Hat (1980) and Carry On (1982). For the album Carry On, Caldwell played all the instruments, was the producer and helped with arranging and mixing. In 1983, Caldwell released August Moon only in Japan. It was released in the United States in the 1990s.
Singer Boz Scaggs advised Caldwell to write songs for other musicians after TK Records shut down. Caldwell wrote "The Next Time I Fall", which became a hit for Amy Grant and Peter Cetera, along with songs for Scaggs himself, Roy Ayers, Chicago, Natalie Cole, Neil Diamond, Roberta Flack, and Al Jarreau.
On Blue Condition (1996), Caldwell turned from R&B to recording big band arrangements of songs from the Great American Songbook, particularly those sung by Frank Sinatra. He also portrayed Sinatra in tributes to the Rat Pack in Las Vegas. He continued to sing standards on Come Rain or Come Shine (1999), The Consummate Bobby Caldwell (2010) and After Dark (2014). In 2015, he collaborated with record producer Jack Splash on the album Cool Uncle.'
In 2019, the owner of the rights to the Caldwell song "Carry On" (from the album of the same name) sued Lil Nas X for $25 million for using the song without permission in his own song of the same name from his 2018 mixtape Nasaratti, which at the time was available on YouTube, Spotify and SoundCloud.
Following Caldwell's death, his 1978 hit song "What You Won't Do for Love" experienced a surge in popularity on social media, such as on TikTok and Instagram. In early 2024, the song reached No. 1 on the TikTok Billboard Top 50 chart as well as a brief entry at No. 86 on the UK Singles Downloads Chart. This was due to a viral trend featuring videos of chocolate-covered strawberries paired with the song's signature horn intro.
Aside from a minor role in 1988's Salsa, Caldwell portrayed Frank Sinatra from October 1999 to January 2000 in the Las Vegas musical The Rat Pack Is Back.
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