History of Bobby Caldwell in Timeline

By Popular Timelines Editorial Team · Updated: February 28, 2025

Bobby Caldwell (1951-2023) was an American singer and songwriter celebrated for his versatile vocals spanning R&B, soul, jazz, and adult contemporary genres. His signature song, "What You Won't Do for Love," from his debut album became a hit in 1978. While releasing several albums in R&B and smooth jazz, Caldwell later transitioned to singing standards from the Great American Songbook. He also wrote songs for other artists, most notably co-writing "The Next Time I Fall". His work has been sampled by numerous hip hop and R&B artists.

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Full Timeline

August 15, 1951: Birth of Bobby Caldwell

On August 15, 1951, Robert Hunter Caldwell, known as Bobby Caldwell, was born. He later became an American singer and songwriter known for his work in R&B, soul, and jazz.

Others born on this day/year

1977: Years in Los Angeles

By 1977, Caldwell had spent six years in Los Angeles playing in different bar bands and trying to get a record deal.

1978: Release of "What You Won't Do for Love"

In 1978, Caldwell released his hit single "What You Won't Do for Love" from his double platinum debut album Bobby Caldwell. This song became his signature song.

1978: Signing with TK Records and Writing "What You Won't Do for Love"

In 1978, Caldwell signed with TK Records in Miami. After recording songs for his first album, he wrote "What You Won't Do for Love" in two days, which became a hit song. Executives at the label wanted to conceal that Caldwell was white, so they kept his face off the album cover.

1980: Release of Cat in the Hat

In 1980, Caldwell released his album Cat in the Hat.

1982: Release of Carry On

In 1982, Caldwell released his album Carry On, for which he played all the instruments and served as the producer, arranger, and mixer.

1983: Release of August Moon

In 1983, Caldwell released the album August Moon only in Japan. It was later released in the United States in the 1990s.

1984: Recording "Never Give Up" for Night of the Comet

In 1984, Caldwell recorded the song "Never Give Up" for the film Night of the Comet.

1988: Minor Role in Salsa

In 1988, Caldwell had a minor role in the film Salsa.

1996: Release of Blue Condition

In 1996, Caldwell released Blue Condition, where he transitioned from R&B to recording big band arrangements of songs from the Great American Songbook.

1998: Caldwell Remakes "What You Won't Do for Love"

In 1998, Caldwell remade his hit song "What You Won't Do for Love".

October 1999: Portrayal of Frank Sinatra

From October 1999 to January 2000, Caldwell portrayed Frank Sinatra in the Las Vegas musical The Rat Pack Is Back.

1999: Release of Come Rain or Come Shine

In 1999, Caldwell released Come Rain or Come Shine, continuing his focus on singing standards.

January 2000: Portrayal of Frank Sinatra

From October 1999 to January 2000, Caldwell portrayed Frank Sinatra in the Las Vegas musical The Rat Pack Is Back.

2000: "Open Your Eyes" sampled by J Dilla

In 2000, the track "Open Your Eyes" from Cat in the Hat was sampled by J Dilla on Common's "The Light".

2001: Song appearance in Simone

In 2001, Caldwell's version of a big band standard appeared in the film Simone.

2002: Song appearance in Lake Boat

In 2002, Caldwell's version of a big band standard appeared in the film Lake Boat.

2006: "What You Won't Do for Love" on American Idol

In 2006, Elliott Yamin covered "What You Won't Do for Love" during the fifth season of American Idol.

2010: Release of The Consummate Bobby Caldwell

In 2010, Caldwell released The Consummate Bobby Caldwell, continuing to sing standards from the Great American Songbook.

2014: Release of After Dark

In 2014, Caldwell released After Dark, continuing to sing standards.

2015: Collaboration on Cool Uncle

In 2015, Caldwell collaborated with Jack Splash on the album Cool Uncle.

2017: Health Decline Due to Medication

In 2017, Caldwell's health began to decline after he suffered severe side effects from fluoroquinolone.

2018: Lil Nas X Mixtape Nasaratti

In 2018, Lil Nas X released the mixtape Nasaratti which at the time was available on YouTube, Spotify and SoundCloud.

2019: Lawsuit against Lil Nas X

In 2019, Lil Nas X was sued for $25 million for using the song "Carry On" without permission.

March 14, 2023: Death of Bobby Caldwell

On March 14, 2023, Bobby Caldwell passed away at the age of 71 at his home in Great Meadows, New Jersey. His health had declined after suffering severe side effects from fluoroquinolone in 2017.