Obeidallah was born in Lodi, New Jersey, and grew up in nearby Paramus.His father was born in Battir, Palestine prior to the creation of the State of Israel, his mother's parents were born in Sicily. Obeidallah received a J.D. from Fordham Law School and practiced law from 1993-1998 with the firm of Beattie Padovano. His first stand up comedy show was as part of the NJ Bar Association's stand up comedy show. He then left the practice of law and was accepted into the prestigious NBC Page program in 1998. Thereafter from October 1999 through May 2007 he was a rights and clearance researcher for Saturday Night Live while performing stand up comedy in the comedy clubs of New York City.

Dean Obeidallah is an American Muslim of Palestinian-Italian descent who left his career as a lawyer to become a political comedian and commentator. He is also a producer, director, regular contributor at CNN and Daily Beast, and host of SiriusXM radio's ‘The Dean Obeidallah’ show, which is the only daily national radio show hosted by a Muslim American. “We're doing this for the next generation of Muslim-Americans, so they grow up in a country where they're not treated less than American.“ Obeidallah has used comedy and the internet as an avenue to highlight issues affecting Muslims. He co-created Stand up for Peace, a comedy show aimed at fostering understanding and supporting a peaceful solution to the Palestinian-Israeli conflict, was Executive Producer of the first stand up comedy festival in the history of the Middle East outside of Israel, co-directed and co-produced an award winning documentary that focuses on freedom of religion for Americans, and has been featured on Comedy Central on the critically acclaimed "Axis of Evil" Comedy special amongst numerous other national and international television programs. In addition to amassing an online fan following and YouTube views of his performances, Obeidallah has also created waves in the digital space as the founder and editor of the blog ‘The Dean’s Report’, which addresses topics of the day.

He is a contributor to CNN, and his work has also appeared in various publications, including The New York Times, Los Angeles Times and Newsweek