Ben Hersey

Dante Milestone, a world-weary baby-boomer, is not happy. His struggles with everyday life, his past, even the question of 'the existence of a higher power', have led him to evaluate his own life. An assessment, that ultimately drives him to leave work and success behind, and set out on a quest in search of his happiness. But Dante soon learns that it's not that simple, for after a series of painfully humorous attempts fail to provide an answer, Dante sinks even deeper. It is not until he encounters Cynthia, a spiritual guide of sorts, that he uncovers the underlying truth and finally arrives at an answer that surprises even him.

A successful New York architect with a beautiful wife and an adoring young son is forced to reevaluate his outwardly idyllic life after a chance meeting with an urban designer reveals the cracks in the foundation of his paradise.

The Worst Kind of Thoughtful is the first comedy special of its kind. Based on the 2018 comedy album by Mike Vecchione, it stars actors, artists, friends, fans, and many of your favorite comedians. It's the first User Generated Comedy Special.