Benjamin began his career developing pieces inspired by reggae music. In 2007, he auditioned for the
second season of ''America's Got Talent'', conducting several songs with his reggae-inflected music; his first for his audition earned praise from
Piers Morgan, a judge for the program at the time, who praised his version of "
Walking on the Moon" as being far better than when it had been sung by the musician
Sting. In June 2010, Benjamin toured Hawaii with
Josh Heinrichs playing shows in
Hawaii, in which he made appearances on several local radio programs and the television morning news portion of
Hawaii News Now. Three months later, he signed a deal with Easy Star Records, who released his follow-up album,
Connection, on September 14. It reached No. 2 on
Billboard's Reggae Albums chart in 2010. Benjamin released his third album,
La Si Dah, on May 28, 2013, which consisted of thirteen songs, funded by his fans, and produced by both Benjamin and Grammy-winning producer-engineer
Rob Fraboni. The release was followed by a European tour. The following year, on November 6, he released the album
More Music More Family on
Jimmy Buffett's
Mailboat Records. In 2020, Cas Haley was the grand prize winner of the
Lincoln Motor Company's "Chart Your Course" contest. His winning song, "Every Road I'm On," beat out over 1,600 entrants. Haley won a talent contract and a recording session at
Capitol Studios, a
Lincoln Corsair, and appeared in a national Lincoln marketing campaign. As part of the promotion, Haley met and worked with actor
Matthew McConaughey, and musicians
Jon Cleary, Tank of
Tank and the Bangas,
Ruthie Foster, and more. Lincoln filmed his cross-country journey, which ended at Capitol Studios in Hollywood, where he recorded the song. The campaign includes a national broadcast and online spot and a 24-minute documentary. "Every Road I'm On" was included on Cas Haley's album,
All the Right People, released in early 2021 on Jimmy Buffet's label, Mailboat Records. ==Personal life==