In 2014, Drew began his stand-up career quickly, making a name for himself around New England, thanks to his quick wit, voice, and unique style. After winning the Boston Comedy Festival in 2017, he began to perform Comedy regularly around the country. In 2018, Drew won the Seattle International Comedy Competition and was selected to be a “New Face of Comedy” at the prestigious Just for Laughs Comedy Festival in Montreal in 2019. Drew has since continued to headline comedy clubs across the US and Canada while making various types of online content, earning millions of views. Drew has a special on Dry Bar Comedy and a set recorded with Don’t Tell Comedy. He has also gained the attention of some of the biggest names in Comedy, including a shoutout on the Joe Rogan Experience. Most recently, Drew opened for comedy legend Dane Cook on his 2023 and 2024 tours.