Len Stein is a Jewish lawyer that handles the will of Loretta Brown in "You're the Best Man, Cleveland Brown". He is employed at Stein & Sons Law Offices and seems to enjoy bagels. While he does rely on a strict interpretation of wills, he also seems to be easily bored by them, skipping over large parts of them and employing gimmicks such as employing Herbert to keep things interesting.
In "American Prankster", he attempts to defend Rallo in court after he is arrested for distributing nude pictures of Cleveland Brown Jr.. Although it's later revealed that he is in on a prank by Cleveland to scare Rallo for his pranks.
Len accompanies Cleveland as he tries to apologize to the public for passing himself off as homeless in "'Tis the Cleveland to be Sorry" but points out every time Cleveland manages to offend a particular group of people including Native Americans, midgets, Interracial couples and pedophiles.
Len Stein is voiced by Glenn Howerton.
- TCS108 From Bed to Worse (Mentioned)
- TCS111 Love Rollercoaster (Mentioned)
- TCS117 Gone with the Wind
- TCS119 Brown History Month (Mentioned)
- TCS121 You're the Best Man, Cleveland Brown
- TCS304 Skip Day (Mentioned)
- TCS317 American Prankster
- TCS406 'Tis the Cleveland to be Sorry
- TCS416 Who Done Did It? (mentioned)