Wolpert's first major exposure ensued after he auditioned for the fifth season of The Voice. In his blind audition, Wolpert sang "Love Interruption" by Jack White and impressed all four judges Christina Aguilera, Cee Lo Green, Adam Levine and Blake Shelton to turn their chairs, signifying their interest in him joining their team. Ultimately, Wolpert chose to join the team of Adam Levine. Subsequently, he sang "Radioactive" against Will Champlin in the battle round, which he won. After that, despite his self-described "atrocious" performance, he advanced in the knockout round singing "More Than a Feeling" by Boston. Wolpert commented, "I picked the song because it's super challenging ... as I got on stage, something just went wrong. I am my own worst critic, so I completely recognize it was atrocious [compared] to what it could have been." Nevertheless, Levine chose him to advance, and he moved on to the first live show, singing "A Case of You", which received rave reviews, and was the winner of the "iTunes Bonus" on the show, as his performance was in the top ten of the most downloaded songs on iTunes. Thus, his iTunes votes from the public were multiplied by five, and ultimately, he advanced to the next round. The following week, he sang "Mr. Brightside" by The Killers, advancing to the top 10. After having to wait until the very end of the show in order to hear that he was saved, he was the first contestant that was saved in the results show the night after he sang "Without You" by Badfinger. A week later, he sang Queen's "Somebody to Love", and a night later, found out he advanced to the top six. The next week would be the most dramatic of the show to that point. After waking up Monday, December 2, the day of the performance, with little voice, he did not talk all day, and sang two songs, I'd Do Anything for Love (But I Won't Do That) and Fell in Love with a Girl, like each of the other Top Six. The next night, he was in the bottom two on the results show, but was saved from the Twitter save over fellow Pennsylvanian Matthew Schuler, and advanced to the next round. On December 10, 2013, Wolpert finished in fourth place along with Cole Vosbury from Team Blake.
- Studio version of performance reached the top 10 on iTunes