Kennedy started off his career in singing in 2011, at age 19, he performed pop and rhythm and blues. He got encouraged by his college friends hence pursuing singing after hearing him sing along to the radio, and he entered a charity contest during which he was well-received. He released an EP, Take Me to the River in 2016, he as well released other singles.
He began to start a Kickstarter campaign to fund the project. Beginning in 2017, He as well collaborated with John Crist. The pair of comedians have released several viral videos, including one about bachelorette parties in Nashville. He as well joined Crist on several of his 2018 tour dates. Kennedy has also done several collaboration videos with King Bach.
He started began hosting a podcast, Correct Opinions with Trey Kennedy, which is produced by Studio71 as of 2019. According to Chartable, the podcast has been in the top 100 for comedy podcasts in the United States, Canada, Australia, and Great Britain. He has had stand-up appearances, including a November 2019 appearance in Madison, Wisconsin. Kennedy’s January 2019 video, “Moms”, had over 4.8 million views on Facebook
. Another video of his that mocks middle school students has over 14 million views. The video led him to release more videos about middle school students, and in March 2020, He has released a TV series, Middle School Maddox, in which Kennedy spoofs middle school angst.
