Entertainment The Saddest (Real) Celebrity Encounters  

Jessica L. Yarbrough
183.8k votes 31.3k voters 4.6M views 22 items

List Rules Vote up the most pathetic real celebrity encounters.

We all love to hear celebrity anecdotes—they make us feel like we really know our Hollywood idols. Celebrity stories can go one of two ways, though: They can bolster our love or they can crush our dreams. A Reddit thread asked users to spill their saddest celebrity encounters. From mean celebrities (Gene Simmons is NOT a nice guy) to just plain sad celebrities (drunken Carrot Top isn't funny anymore), here are the saddest celebrity encounters of all time—that really happened!

Once you've cringed at the stories on this list, be sure to read all about the celebrities who were jerks even before they had fame in their corner.

Betty White is listed (or ranked) 1 on the list The Saddest (Real) Celebrity Encounters
Photo:  David Shankbone/Wikimedia Commons/CC BY 2.0

Betty White is all of us in this moment from joeb7474: "I was at the Beverly Center in Los Angeles and saw a poster promoting Betty White signing her latest book about how much she loves animals. I liked the Golden Girls so I thought I would swing by the bookstore to take a gander at Betty White. It was so sad. I'll always remember she was sitting alone at a big table with a stack of books in front of her. People were in the bookstore shopping but no one was buying her book or really acknowledging her. She just sat there, pen in hand, waiting. She would occasionally wipe off some imaginary dust to look busy."

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Muhammad Ali is listed (or ranked) 2 on the list The Saddest (Real) Celebrity Encounters
Photo:  pablo.raw/Wikimedia Commons/CC BY-SA 2.0
GretSeat got a chance to meet his hero, Muhammad Ali, at a restaurant in Florida and asked for his autograph. "He took at least (no joke) 2 full minutes to sign his name. And it was at that point that it killed me. This was Cassius Clay. Muhammad Ali. The most charismatic, float like a butterfly sting like a bee, man in boxing history. And he was such a shell of his former self because of the Parkinson's. It was so heartbreaking. It really was."

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#86 on The Most Trustworthy Celebrities in the World

#87 on The Most Important Leaders in U.S. History

#19 on The Best Boxers of the 20th Century

#2 on The Toughest Professional Fighters in History

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Steve-O is listed (or ranked) 3 on the list The Saddest (Real) Celebrity Encounters
Photo: Gage Skidmore/Wikimedia Commons/CC BY-SA 3.0
Willie1707 went to see Steve-O do stand up and said, "After his show, he said he would meet everybody there. We waited in line, and he was being super nice, laughing and taking pictures with everyone. Right before we got to the stage some fat, redneck a**hole told him that he was funnier back when he was on drugs. It killed his whole vibe. When we got to him he just took a picture with us and said thanks for coming, but he was clearly in a bad mood."

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#11 on The Best Comedians On Joe Rogan

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Demi Lovato is listed (or ranked) 4 on the list The Saddest (Real) Celebrity Encounters
Photo:  Frank Schwichtenberg/Wikimedia Commons/CC BY-SA 4.0

When Redditor kateyrnabbcan4 and her 9-year-old younger sister saw Demi Lovato sitting a few booths away at a local restaurant, they decided to ask for a picture. "My sister walked over on her own and I sat and watched Demi tell her something along the lines of 'No, can't you see I'm f*cking busy?!' My sister came back to me in tears and we immediately paid for our unfinished food and left, because she was so upset."

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#10 on The Best Current Female Singers

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