Hollywood The Most Entertaining Celebrity Trainwrecks of All Time  

Celebrity Lists
9.3k votes 1k voters 165.5k views 26 items

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.
1 610 VOTES

Charlie Sheen

Ranker Video
Video: YouTube
In the wake of his 2011 firing from the hit CBS sitcom "Two and a Half Men," and a fallout with series' creator Chuck Lorre, Charlie Sheen had a very public meltdown in which he proclaimed he was a "warlock" who had "tiger blood" and "Adonis DNA" flowing through his veins. Hollywood's most famous bad boy even shacked up with two female porn stars he collectively nicknamed his "goddesses" and started the viral hashtag #WINNING. Sheen returned to series TV the following year with a starring role on FX's "Anger Management."

Age: 52

Birthplace: New York City, New York, United States of America

Also Ranked

#54 on Celebrities with the Weirdest Middle Names

#91 on If You Fought To The Death, Who Would You Want By Your Side?

#63 on The Most Psychedelic People Ever

#16 on The Greatest '80s Teen Stars

458 152
see more on Charlie Sheen
2 664 VOTES

Kanye West

Kanye West is listed (or ranked) 2 on the list The Most Entertaining Celebrity Trainwrecks of All Time
Photo: via Imgur
The outspoken rapper and Kim Kardashian's baby-daddy has had so many public outbursts that garnered him his own list of Kanye West's famous rants and stage crashes.

Age: 40

Birthplace: Atlanta, Georgia, United States of America

Also Ranked

#13 on The Best New School Rappers

#10 on The Greatest Rappers of All Time

#41 on The Best Rap Lyricists of All Time

#10 on The 25+ Best Rappers Of 2018, Ranked

491 173
see more on Kanye West
3 586 VOTES

Lindsay Lohan

Lindsay Lohan is listed (or ranked) 3 on the list The Most Entertaining Celebrity Trainwrecks of All Time
Photo: via Wikimedia
Lindsay Lohan's infamous collection of mugshots only tells half the story. Considered the ultimate Hollywood trainwreck, the former child star turned into a cautionary tale with her multiple arrests, rehab stints, jewelry thefts, family drama, and reckless driving. Lohan also went from starring in beloved movies such as The Parent Trap and Mean Girls, to cinematic crapfests like The Canyons and Liz & Dick.

Age: 29

Birthplace: New York City, New York, USA

Also Ranked

#64 on The Greatest Former Child Stars

#20 on Everyone Is Talking About New York Con Artist Anna Delvey, So Who Should Play Her In The Show?

#17 on Celebrities You'd Want To Go To Vegas With

#5 on The Celebrities You Most Want To See Play Survivor

437 149
see more on Lindsay Lohan
4 514 VOTES

Courtney Love

Courtney Love is listed (or ranked) 4 on the list The Most Entertaining Celebrity Trainwrecks of All Time
Photo: via Reddit
The queen of grunge has cleaned up her lipstick-smeared act every once in awhile, but these days she's known for her bizarre Tweets, her ongoing feud with former Nirvana member Dave Grohl, and her estrangement from daughter Frances Bean.

Age: 53

Birthplace: San Francisco Peninsula, Northern California, California, Contiguous United States, San Francisco Bay Area, + more

Also Ranked

#49 on The Best Female Rock Singers

#9 on The Druggiest Rock Stars of All Time

#89 on The Greatest Women in Music, 1980s to Today

#38 on Celebrities Who Get A Way Worse Rep Than They Deserve

354 160
see more on Courtney Love