drugs The Most Depressing Celebrity Trainwrecks of All Time  

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List of the most depressing celebrity trainwrecks of all time. These sad tales of tragedies and unfortunate turns in the lives of stars are just a small glimpse into the price of fame. Unlike the most entertaining celebrity trainwrecks, the famous people featured in the list endured personal hardships and battled inner demons that caused sadness and grief to their family, friends, and millions of fans all over the world. The list includes rock and pop music royalty, former child stars, and even the sexiest women in Hollywood. Most of the most heartbreaking stories of celeb train wrecks end up in the untimely death of a star, whether they died at a young age or just when their career was just taking off.

Global superstars like Michael Jackson and Whitney Houston often made headlines not just for their music and career, but also for their personal battles with addiction and other personal issues. These senseless, shocking, and devastating stories show that the rich and famous are not exempt from pain, sadness, and tragic consequences. Most, if not all, the stars on this list of depressing Hollywood trainwrecks continue to be a part of people's lives, even though some of them have passed away. They have even become legends of music, film, and pop culture because of their downward spiral. Meanwhile, other internationally renowned celebs like Britney Spears and Matthew Perry were able to overcome their battles and return to a sober, more normal life outside of the spotlight.

Who is the most depressing celebrity trainwreck of all time? Vote up for your pick from the list and see how other Ranker members voted. If you really want to feel even more depressed, check out this list of celebrity members of the 27 Club and list of musicians who died in plane crashes.
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John Belushi


John Belushi is listed (or ranked) 1 on the list The Most Depressing Celebrity Trainwrecks of All Time
Photo:  uploaded by Celebrity Lists
For years, John Belushi was known to friends and Hollywood was as a fun loving guy who enjoyed life. His appetite for partying eventually did him in, though. Overdosing on a speedball (cocaine and heroin) in 1982 ended the life of one of modern comedy's great talents and superstars. His death left a lot of "what ifs?" about his career.

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Age: Died at 33 (1949-1982)

Birthplace: Humboldt Park, Chicago, Illinois, United States of America

Profession: Comedian, Musician, Screenwriter, Actor

Credits: The Blues Brothers, Saturday Night Live, Animal House, 1941

Also Ranked

#12 on The Funniest People of All Time

#3 on The Best SNL Cast Members of All Time

#45 on People We Wish Were Still Alive

#25 on The Greatest Rock Stars Who Died Before 40

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Chris Farley


Chris Farley is listed (or ranked) 2 on the list The Most Depressing Celebrity Trainwrecks of All Time
Photo:  uploaded by Celebrity Lists
While "Saturday Night Live" and Tommy Boy made him a household name by 1995, Chris Farley became increasingly dependent on drugs and food in the last years of his life, appearing at public events notably intoxicated. He reportedly sought treatment for obesity and drug abuse 17 separate times. In December 1997, Farley was found dead of an overdose of cocaine and morphine at just 33 years old.

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Age: Died at 33 (1964-1997)

Birthplace: Madison, Wisconsin, United States of America

Profession: Stunt Performer, Comedian, Actor

Credits: Tommy Boy, Beverly Hills Ninja, Black Sheep, Wayne's World 2

Also Ranked

#11 on The Funniest People of All Time

#1 on The Best SNL Cast Members of All Time

#96 on People We Wish Were Still Alive

#35 on Which Actor Would You Bring Back for One Final Movie?

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Whitney Houston


Whitney Houston is listed (or ranked) 3 on the list The Most Depressing Celebrity Trainwrecks of All Time
Photo:  uploaded by Celebrity Lists
A voice unlike any other, Whitney Houston's life was silenced to a longtime battle with addiction that ultimately caused her untimely death in 2012. For years, Houston's drug and alcohol abuse was well chronicled. Appearing on the "Being Bobby Brown" reality show and her gaunt appearance at the Michael Jackson tribute show in 2001 raised eyebrows. Houston's life and legacy was honored the night after her death at the Grammy Awards.

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Age: Died at 49 (1963-2012)

Birthplace: Newark, New Jersey, United States of America

Profession: Record producer, Songwriter, Musician, Film Producer Model, + more

Credits: The Bodyguard, Waiting to Exhale, The Preacher's Wife, Whitney Houston: The Greatest Hits

Also Ranked

#5 on The Best Singers of All Time

#27 on The Best Current Female Singers

#1 on The Best Female Vocalists Ever

#7 on The Female Singer You Most Wish You Could Sound Like

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Judy Garland


Judy Garland is listed (or ranked) 4 on the list The Most Depressing Celebrity Trainwrecks of All Time
Photo:  skeeze/Pixabay/CC0 1.0
Hollywood icon Judy Garland was found dead by her fifth husband, Mickey Deans, at their rented London home in 1969. The cause of death was described as "an incautious self-overdose" of barbiturates.

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Age: Died at 47 (1922-1969)

Birthplace: Grand Rapids, Minnesota, United States of America

Profession: Actor, Vaudeville Performer, Singer

Credits: The Wizard of Oz, Meet Me in St. Louis, Easter Parade, A Star Is Born

Also Ranked

#26 on The Best Actresses in Film History

#89 on The Greatest Actors & Actresses in Entertainment History

#26 on The Best Female Vocalists Ever

#7 on The Greatest American Actresses of All Time

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Amy Winehouse


Amy Winehouse is listed (or ranked) 5 on the list The Most Depressing Celebrity Trainwrecks of All Time
Photo:  uploaded by Celebrity Lists
Her distinctive voice and throwback to a long-gone era made Amy Winehouse a musical powerhouse, but her drug and alcohol addiction proved far stronger than everything else. For years, Wino was as well known for her drug addiction as she was for her powerful voice. Her behavior was erratic and made her a fixture in the tabloids. Eventually, and sadly unsurprising, Winehouse joined the infamous 27 Club when she died in 2011.

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Age: Died at 28 (1983-2011)

Birthplace: Southgate, London, London, United Kingdom

Profession: Arranger, Musician, Singer-songwriter

Credits: About Time, The Great Gatsby, Amy, Life as We Know It

Also Ranked

#29 on The Best Singers of All Time

#16 on The Best Female Vocalists Ever

#2 on The Female Singer You Most Wish You Could Sound Like

#16 on The Greatest Singers of the Past 30 Years

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29 people just voted on Janis Joplin


Janis Joplin is listed (or ranked) 6 on the list The Most Depressing Celebrity Trainwrecks of All Time
Photo:  uploaded by Celebrity Lists
The queen of psychedelic rock and soul, Janis Joplin overdosed on heroin combined with alcohol. Before her death, besides being known as one of the great vocalists in music, Joplin had a raging drug habit. She was posthumously inducted into the Rock and Roll Hall of Fame in 1995, 25 years after her death.

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Age: Died at 27 (1943-1970)

Birthplace: Port Arthur, Texas, United States of America

Profession: Songwriter, Singer

Credits: Three Kings, The Dreamers, Watchmen, Little White Lies

Also Ranked

#52 on The Greatest Musical Artists of All Time

#17 on The Best Rock Vocalists

#36 on The Best Singers of All Time

#15 on The Best Female Vocalists Ever

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Anna Nicole Smith


Anna Nicole Smith is listed (or ranked) 7 on the list The Most Depressing Celebrity Trainwrecks of All Time
Photo:  uploaded by Celebrity Lists
Curvaceous and buxom blonde beauty Anna Nicole Smith was often compared to Marilyn Monroe early in her career, but the price of fame soon took its toll. Smith's crazy life was caught on tape through her popular reality show, but the darker side of her personal struggles played out during the last few years of her life, from her son Daniel's death, a publicized paternity suit for her daughter, and an addiction to prescription drugs. Smith was found dead of a drug overdose in 2007.

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Age: Died at 40 (1967-2007)

Birthplace: Texas, United States of America

Profession: Spokesperson, Stripper, Adult model, Film Producer Model, + more

Credits: The Anna Nicole Show, Anna Nicole Smith: Exposed, Playboy Video Centerfold: Playmate of the Year Anna Nicole Smith, Playboy Video Playmate Calendar 1994

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Jim Morrison


Jim Morrison is listed (or ranked) 8 on the list The Most Depressing Celebrity Trainwrecks of All Time
Photo:  uploaded by Celebrity Lists
For years, Jim Morrison was known as one of the sexiest men not only in rock, but in the world. Unfortunately, though, The Doors frontman's drinking got out of hand, and the Lizard King eventually succumbed to the alcoholism that marked his later tumultuous days. He died of heart failure in 1971 at age 27 while living in Paris.

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Age: Died at 28 (1943-1971)

Birthplace: Melbourne, Florida, United States of America

Profession: Film Score Composer, Poet, Songwriter, Musician Screenwriter, + more

Credits: Cast Away, The Doors, Minions, Girl Interrupted

Also Ranked

#5 on The Best Rock Vocalists

#28 on The Best Singers of All Time

#4 on The Best Frontmen in Rock

#2 on The Greatest Musicians Who Died Before 30

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