1. Artie Lange
When one thinks of very public falls from grace, Artie Lange’s story rings hauntingly in our memory. In the mid-1990s, Lange was a highly respected comedian on top of his game. He was pulling big laughs on the seminal sketch comedy show MadTV during its first season, and eventually took things to the next level.
When The Howard Stern Show was at its height, Artie Lange was one of the best aspects of the show. One can’t even count the number of classic segments that involved Artie. However, a long-time substance abuse problem would continuously come back to disrupt his flow. It’d eventually tank his career; Lange went broke, with much of his cash being eaten up as a consequence of his addictions.