Toby Keith's Tour Challenge

Toby Keith photo courtesy of Show Dog Nashville.

June 23, 2008 — This month marks 15 years since Toby Keith earned his first No. 1 hit with "Should’ve Been A Cowboy," and while plenty of other artists have had hits and then faded in that period, Toby’s still right there getting his name in the Top 10.

It creates a bit of a problem for his live show, though it’s a problem that every artist would like to have.

"My show's almost two hours long, and that's still not enough time to play [all the hit] songs," Toby told The Charlotte Observer. "I've sold 30 million albums, and this is my 15th album. If there are three or four singles off of each album, you're talking 45 or 50 songs, and you're getting to where you just can't do them all. You just try to make the most sense of a song list, and then you try to mix in a few new ones."

Ultimately, the songs Toby is able to fit into the set list are all designed to get the crowd active and sweaty.

"We’re very live, we’re very energetic," Toby said. "We sell a good time. We don’t try to bring the beach to you, we don’t try to bring a circus to you. We try to bring a rowdy, hot, good time to make you feel good."

To that end, Toby enlisted Montgomery Gentry for this summer’s Biggest & Baddest Tour, which launched last week in Alabama. The lineup also features three acts signed to Toby’s label, Show Dog Nashville: Carter’s Chord, Trailer Choir and Mica Roberts. The tour’s in the Southeast this weekend, playing West Palm Beach on Friday, Tampa on Saturday, and Charleston, S.C., Sunday.