Touched by an Angel (1994)

S8E7 Most Likely To Succeed

Dennis Loggins, a young billionaire, has transformed himself into a fit, successful man, claiming his achievements are all for the love of a wonderful woman. However, the truth is he has meticulously crafted this image as a means of revenge. In high school, he was an awkward nerd infatuated with the popular cheerleader, Melissa, whose kindness only deepened his feelings. Unfortunately, he was relentlessly bullied by Melissa's boyfriend, Ricky, who famously exposed Dennis's crush during a live football game announcement. Despite Melissa's comforting words, the embarrassment lingered. Now, with a successful life in his hands, Dennis seeks to settle the score, enlisting Gloria as his assistant to uncover which football team Ricky plays for and plot his revenge.