Henry Zebrowski attended Florida State University in Tallahassee, Florida where he began to perform as a comedian, initially in the group "Oncoming Traffic", later in "Girls Aren’t Funny", which was renamed to "Murderfist", alongside his sister, Jackie Zebrowski. The group had a weekly show in a gay bar.

In 2006, Zebrowski moved to New York City, where he continued to perform as a comedian. Since 2009 he has had minor roles in TV shows and series such as Law & Order: Special Victims Unit and Blue Bloods. In 2010 he had a role in the drama White Irish Drinkers.

In 2013, Zebrowski played the role of Alden "Sea Otter" Kupferberg in Martin Scorsese's The Wolf of Wall Street.

In 2015, Zebrowski appeared in The D Train starring Jack Black.

From 2011 to the present, Zebrowski has been a member of the horror/comedy podcast, "Last Podcast on the Left", alongside Marcus Parks and Ben Kissel. Zebrowski has also featured on many other Cave Comedy Radio podcasts. The trio also began "Last Stream on the Left" on Adult Swim in 2016.

He is also known for his work on the Adult Swim series Your Pretty Face Is Going to Hell.

In March 2015, it was announced that Zebrowski would have a recurring role on the NBC TV series Heroes Reborn. His role was Quentin Frady, a conspiracy theorist.

In 2016, he wrote and starred in his own 30-minute episode of the sketch show Netflix Presents: The Characters.

Comedians, Comedy, Television Comedy, Sketch Comedy, Podcaster, Actors, Entertainment Industry, Acting, Modern Media Standup Comedy, Entertainment,