Taylor Swift launched her successful music career in 2006 — and she has a surprising connection to the late Toby ... debut, self-titled album after striking a deal with Big Machine Records ...

Toby Keith is the subject of a star-studded celebration ... gave him a signed CD copy of his eponymously titled debut album ...

and performing “My List” during the Toby Keith: American Icon tribute show. Keith released “Should’ve Been A Cowboy” on his self-titled debut album in 1993. He became known for that song ...

Jason Aldean paid tribute to Toby Keith at the 2024 ACM Awards, performing a elegantly low-key version of "Should've Been a Cowboy," Keith's 1993 debut single, backed by a string quartet.