Cronin switched careers permanently when he joined Howard Stern's nationally syndicated Saturday night television show The Howard Stern Show as a staff writer in 1991.[2] His responsibilities expanded to include scripting entire episodes, producing celebrity interviews, and producing comedic field pieces.[3] He went on to contribute to Stern's national radio show [citation needed] and serve as producer/writer on his television and video projects, including Stern's New Year's Rotten Eve pay per view special[4] — the most watched entertainment pay per view event of all time.[5] Cronin also scripted an entire E! Entertainment special for Stern's book, Miss America.[6]
In 1995, he moved to Los Angeles to become head writer for MTV's dating show Singled Out with Chris Hardwick and Jenny McCarthy. He eventually was promoted to show-runner for two seasons. In 1996, he joined the Fox network, supervising production for their first prime-time game show, Big Deal. In 1997, he returned to late night and served as supervising producer for The Keenen Ivory Wayans Show.[citation needed]
In 1997, Cronin founded Mindless Entertainment with then-partner Gary Auerbach, who left the company in 2001. The inspiration for the company name came from Cronin's mother, who called TV "that mindless entertainment".
In 2014, Cronin began producing under a new banner, Little Wooden Boat Productions. Under Little Wooden Boat, he became executive producer of Idiotest on Game Show Network. Idiotest premiered its fourth season, Thursday, January 19, 2017.[14]
As of 2024, Below Deck has had continued success[15][16] with its audience and has completed eleven seasons. Season 4 was one of Bravo's fastest growing series [17] and season 11 just finished a successful run in early 2024.
With Below Deck's popularity, Cronin sold a spin-off show to Bravo called, Below Deck Mediterranean.[18] This series premiered May 3, 2016 and the season's ratings permitted Bravo to renew the show for a second season that premiered in 2017.[19]
