hollywood The Most Entertaining Celebrity Trainwrecks of All Time
List of the most entertaining celebrity trainwrecks of all time. From self-destructive behavior, to bizarre appearances, to just plain kookiness, the following famous people are known for stirring up controversy and keeping the tabloids alive. The troubled exploits of the rich and famous always gets attention and it's impossible not to keep looking or following the star's every crazy move. This list of awesome superstar trainwrecks includes possibly STD-riddled celebs, the hottest hot messes of all time, and even some of the druggiest rock stars in history.
The rise of social media has even helped these crazy celebs to crank up the level of insanity to high gear. This is because of the popularity of Twitter rants, open letters on Facebook, or thousands of Tumblr pages and YouTube videos documenting the highs and lows of living a celebrity life. It's not always funny, especially when the star gets into serious medical or legal trouble, but it doesn't take away the entertainment value of watching real life imitating art. While some of the famous train wrecks and hot messes below have either cleaned up their act or has since passed away, each one has left, in one way or another, a huge mark for injecting heavy doses of scandal and notoriety to Hollywood history.
So who is the Hollywood's most entertaining trainwreck of all time? Cast your vote for the messiest, most scandalous, and craziest celeb in the list below, and see who gets voted to the top! Don't forget to check out these lists of celebrities who have declared bankruptcy and stars with gambling problems.Charlie Sheen

Age: 52
Birthplace: New York City, New York, United States of America
Also Ranked
#16 on The Greatest '80s Teen Stars
#63 on The Most Psychedelic People Ever
#19 on Celebrities Who Deserve Their Own Postage Stamp
#55 on Celebrities with the Weirdest Middle Names

Kanye West
Age: 40
Birthplace: Atlanta, Georgia, United States of America
Also Ranked
#14 on The Greatest Rappers of All Time
#50 on Which Celeb Do You Want as Your Introverted Best Friend?
#57 on Celebrities Whose Lives You Want
#59 on Hip Hop Stars You Most Wish You Could Sound Like
Lindsay Lohan
Age: 31
Birthplace: New York City, New York, United States of America
Also Ranked
#70 on The Greatest Former Child Stars
#19 on Celebrities You'd Want To Go To Vegas With
#5 on The Celebrities You Most Want To See Play Survivor
#7 on People We Want to See on a Comedy Central Roast
Courtney Love
Age: 53
Birthplace: California, United States of America
Also Ranked
#9 on The Druggiest Rock Stars of All Time
#89 on The Greatest Women in Music, 1980s to Today
#50 on The Best Female Rock Singers
#43 on Celebrities You'd Want To Go To Vegas With