is the subject of a star-studded celebration slated for Monday in Nashville. Ever-fascinating about the 20-time country music chart-topper, influential businessman and philanthropist — who died on Feb. 5 after a — is how broad, yet deep were the friendships maintained by the "Should've Been a Cowboy" and "How Do You Like Me Now" singer.

It's logical that some of the performers at Monday's event, such as Luke Bryan, Eric Church, Darius Rucker and Carrie Underwood, should have longstanding relationships with the proud Oklahoman and global superstar. However, there was also Keith's 30-year-friendship with Carrot Top that extended far past the comedian's appearance in the 2011 video for Keith's unexpected hit "Red Solo Cup." In fact, before Keith's February passing, Carrot Top was the last artist to appear onstage and perform alongside Keith.

It was one of many moments shared by the two performers, whose careers broke wide open to American stardom in the early 1990s. Comedians and rising country stars of the era often shared identical tour itineraries. Keith, alongside top country stars like Dierks Bentley, Alan Jackson and Keith Urban and rockers like REO Speedwagon, frequently saw Carrot Top's comic routine of the time, which included the now 59-year-old performer, born Scott Thompson, appearing onstage in drag.

Upon their first meeting, Keith, taking a liking to the fellow rising star — and noting that Thompson's father was a longtime country music fanatic — gave him a.