Bobby Caldwell was born in Manhattan,[3] but grew up in Miami, Florida. His mother sold real estate and one of her clients was reggae singer Bob Marley; Caldwell and Marley became friends. Growing up in Miami exposed Caldwell to a variety of music such as Haitian, Latin, reggae, and R&B. His parents hosted a local variety television show called Suppertime.[4][5] He grew up listening to the music of Frank Sinatra and Ella Fitzgerald.[6] When he was 12, Caldwell started playing piano and guitar. He was drawn to rock and roll, jazz, and rhythm and blues.
Career
Caldwell was a member of a Miami band called Katmandu who wrote much of their material while also performing traditional standards. Caldwell played multiple instruments and sang. At 17, he worked with the band in Las Vegas, then moved to Los Angeles.[3]
Caldwell got his first career break as a rhythm guitarist for Little Richard in the early 1970s.[7][8] Caldwell and his band eventually left Little Richard, and Caldwell went solo.[8] By 1977, he had spent six years in Los Angeles playing in different bar bands and trying to get a record deal.[8] 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.[5][6]
Caldwell's debut album was followed by Cat in the Hat (1980) and Carry On (1982). The track "Open Your Eyes" from Cat in the Hat was sampled by J Dilla on Common's "The Light" from his 2000 album "Like Water for Chocolate".[10] "Open Your Eyes" was also covered by artists John Legend and Dwele. For the album Carry On, Caldwell played all the instruments, was the producer and helped with arranging and mixing.[11] In 2019, Lil Nas X was sued for $25 million for using the song "Carry On" (from the album of the same name) 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.[12] In 1983, Caldwell released August Moon only in Japan. It was released in the United States in the 1990s.
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.[6][14][15] 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.[13]