Natasha Lyonne

The “American Pie” actress was arrested in 2001 for a DUI. In 2004, she was charged with trespassing and harassing a neighbor and doing really creepy things to their pet. She also ended up in the hospital with health complications, and ended up getting evicted. Being broke and problematic, Natasha ended up living in the streets. Today’s she’s back on track, starring on Netflix’s “Orange is the New Black.”