Culture and Lifestyle Celebrities Toby Keith Had The Whole Bar Singing Along To “Should’ve Been A Cowboy” The Oklahoma-born "Red Solo Cup" singer was spotted at a local watering hole after a big basketball game where he was leading the crowd in a singalong. By Melissa Locker Melissa Locker Melissa Locker writes about food, drinks, culture, gardening, and the joys of Waffle House Southern Living's editorial guidelines Published on January 21, 2023 Share Tweet Pin Email Photo: Jason Kempin/Getty Images Toby Keith knows how to celebrate a win—or, for that matter, a loss. The Oklahoma-born "Red Solo Cup" singer was spotted at a local watering hole after a big basketball game where he was leading the crowd in a singalong, even though his team had lost. Oklahoma University and its rival Oklahoma State had battled it out at the Gallagher-Iba Arena in Stillwater with Keith in the audience. While his beloved OU had lost, Keith still went out to a local joint for an afterparty. There, he led a sing-along of “Should’ve Been A Cowboy”, with a massive crowd of students and other fans. In the video shared by the WhiskeyRiff website, Keith can be seen leading a raucous crowd through the song. He even hilariously stops and points at people in the crowd who aren’t getting in on the fun, yelling, “You ain’t singing!” Last year, the "Courtesy of the Red, White and Blue" singer announced his battle with stomach cancer. "I've spent the last six months receiving chemo, radiation, and surgery," Keith told his fans. "So far, so good. I need time to breathe, recover, and relax. I am looking forward to spending time with my family. But I will see the fans sooner than later. I can't wait. -T" It is nice to see Keith “getting back into fighting shape” and having some fun with his fans. Was this page helpful? Thanks for your feedback! Tell us why! Other Submit