In January 2023, Dwight filmed his first comedy special at The Comedy Attic in Bloomington, where he started comedy many moons ago. Most recently, Dwight filmed a set for the circle network which will air on Peacock in the early spring of 2023. In 2018, his self-produced album "Sip and Pass" reached #1 on the iTunes comedy charts, making it his second release to do so. In that same year, he was listed as Indiana’s selection for Thrillist’s 50 Best Undiscovered Comics in the country. Dwight’s comedy has been featured on Kevin Hart’s LOL on Sirius XM and on the Bob and Tom show for which he is also a writer. He is a co-director of the Limestone Comedy Festival and the creator and host of the web-series BrewTube Comedy.