A week after previewing his vocal skills with a short clip of himself singing Taylor Swift's "Shake It Off" in the shower, Wainwright, cowboy hat and all, brought his performance to the Dave & Buster's stage to highlight an evening in which his foundation raised approximately $40,000 for charity.
"I'll do anything -- almost anything -- for donations," Wainwright said afterward. "At the end of the day, my personality has always made me comfortable talking and making a fool of myself in public, on stage, wherever. I am quite good at making a fool of myself."
The actual sing-off competition started with 10 karaoke contestants who won spots via Twitter audition videos. Another five qualified for wild-card spots. They performed songs that crossed several genres, from Christina Aguilera's "What A Girl Wants" to George Strait's "I Cross My Heart" to "Come Sail Away" by Styx.
With Wainwright and Cardinals teammate Lance Lynn serving as judges, the group of singers was trimmed to six and then three before Wainwright awarded the top prize -- $500 in cash and a signed baseball bat -- to 18-year-old Audri Bartholomew.
"Absolutely flawless," was how Wainwright described her final performance.
After accepting her prize, Bartholomew, who aspires to make a career from singing, said she planned to donate part of her winnings to the three charities that benefited from the event.
Sandwiched around the competition were performances by Wainwright, who sang a pair of solos and two duets with members of the audience. Mixing in a few dance moves to enhance his performance, Wainwright registered high marks for entertainment value. He couldn't convince Lynn to join him on stage, but negotiated a generous donation from his teammate in order to let him off the hook.
The highlight of Wainwright's night, though, was the generosity from those in attendance. He paused the competition midway through to highlight the mission of the three charities -- Cardinals Care, Operation Food Search and Crisis Aid -- that were to benefit from the event. By pledging to match any donations made during the intermission, Wainwright raised more than $30,000 within minutes.
That money, Wainwright explained to the crowd, was enough to cover the cost of food for 2,000 children in the St. Louis area and save the lives of 170 malnourished individuals around the world.
"Wasn't that amazing?" Wainwright said as he stepped off the stage. "When I hear those numbers, it makes it come to life, to know that there are going to be 170 people that don't die."
The success of the evening affirmed Wainwright's intention to make this a yearly event.
"When you leave here tonight," Wainwright told the crowd, "you can know that however much fun you had or how many nachos you ate ... just know that after all of that, you [did] some amazing things."