In 2019, Allen won the 2019 BroadwayWorld Cabaret Award for Best Recurring Series for his "An Evening With... Series" as well as the award for Best Special Event (Solo) for Marti Gould Cummings's Marti & The Cummers while also being nominated for Best Musical Director and Best Independent Album, for his An Evening With..., Vol. 1 That same year, Allen also won the 2019 GLAM Award for Best Cabaret for Tina Burner's Witch Perfect at Alan Cumming's Club Cumming along with fellow performers Bootsie Lefaris and Tammy Spenks. In 2020, Allen won Best New Arrangement for Mack the Knife and was nominated for My Funny Valentine, Best Musical Director, and Best Recurring Series for An Evening With... Series. Allen also performed, to rave reviews, at Birdland with Lortel and Drama Desk Award winner Kuhoo Verma in early 2020.
