Freddie Prinze. At 19 he’s an unknown standup comic who gets a shot on the Tonight Show. He then gets the lead in a top-rated TV show, a hit comedy album, a wife and child – and a drug problem. Four years and one month after his big break, he committed suicide.
So, this is a literal fall from Grace. Well, except for the fall part, anyway.
OK, that was evil. I’m really pissed! Cause I didn’t think of it … 
Flip Wilson. He had the edgiest, most respected comedy/variety show of the early 70s (He was the Dave Chappelle of his day). After a drug bust, he lost everything and was later relegated to humiliating bit parts until around 1990. He died in 1998.
Note: All online sources dance around the circumstances of Wilson leaving his hit show in 1974 and I can’t find an online cite that a drug bust was the reason. It was, and it wasn’t his last drug bust, either. Still, other entertainers kept their careers after comparable or worse peccadilloes, and this one sticks out as unduly harsh.
I can see how Britney Spears and Drew Barrymore can be said to have fallen, but how does Angelina Jolie join them? She’s been consistently famous since breaking through with Gia in 1998.
I probably should have said “biggest” rather than “quickest” since Lohan went from respected, on magazine covers for decent reasons, hosted Saturday Night Live - to trashy looking, drugged out, jail denizen, who may never work in major movies again.
but those sports examples may have her beat. Tiger lost a LOT of endorsement money, didn’t he?
Well she got a reputation of being pretty scary for a while after she made out with her brother and wore her husband’s blood around her neck. This stuff happened around the early part of 2000, and while she could still find work, her performances were not being lauded and nominated for awards the way they were prior to her odd behavior. Today, she is once again regarded as a beautiful woman worthy of emulation – certainly much more so than she was ten years ago, and the awards shows like her again.
In terms of critical respect, hard to argue with Cuba Gooding Jr. Who went from Oscar in 1997 to Snow Dogs and Boat Trip in 2002.
He’s had a healthy career, but he hasn’t sniffed Oscar again.
I came in to mention OJ. My second choice is Woody Allen.
While I remember Angelina Jolie being considered kind of a freakshow for a while, it doesn’t seem to have hurt her career even temporarily. Looking at her list of screen credits she starred in a number of major Hollywood films in the early 2000s. While she wasn’t nominated for any big acting awards between Girl, Interrupted (2000) and A Mighty Heart (2008) I’d attribute that more to the fact that she starred in several big action movies (not generally Oscar-bait) and just plain bad movies than because critics were put off by her personal life. I don’t think professional critics care much about whether actors behave strangely when off-camera.
I’m also not sure why you listed Jolie as a former child star like Drew Barrymore when, aside from a brief appearance in one of her father’s movies when she was a kid, Jolie’s career as an actress didn’t begin until she was 18.
[larryking]
“Fatty Arbuckle for the full hour”
[/larryking]
:dubious:
Getting back to the OP: how about Gary Busey?