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U.S. Celebrity Gossip by Year, 1991–2009

For each year, try to guess these mostly-American celebrities who were the subject of a major piece of celebrity gossip.
Please do not whine that British celebrities might make an occassional appearance
Quiz by Quizmaster
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Last updated: November 30, 2023
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First submittedNovember 28, 2014
Times taken36,291
Average score73.7%
Rating3.74
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Year
Gossip
Answer
2009
Singer whose acceptance speech was interrupted by Kanye West in
a shocking act of villainy
Taylor Swift
2008
Singer who divorced English filmmaker Guy Ritchie
Madonna
2007
Football player sentenced to prison for running a dog-fighting ring
Michael Vick
2006
Actor who blamed Jews for all the world's problems after being arrested for DUI
Mel Gibson
2005
Actor who jumped on Oprah's couch to declare his love
Tom Cruise
2004
Disheveled backup dancer who became engaged to Britney Spears
Kevin Federline
2003
Heiress who was famous for being famous - and also for a sex tape
Paris Hilton
2002
Singer who dangled his newborn baby from a hotel balcony
Michael Jackson
2001
"Beetlejuice" star who was arrested for shoplifting
Winona Ryder
2000
Critically-acclaimed actor arrested for cocaine and valium possession
while starring in "Ally McBeal"
Robert Downey Jr.
1999
Actress who got divorced from tennis star Andre Agassi
Brooke Shields
1998
Intern that Bill Clinton said he did not have sexual relations with,
before admitting that he did
Monica Lewinsky
1997
Princess who died in a car crash in Paris
Princess Diana
1996
Woman whose brief marriage to Michael Jackson came to an end
Lisa Marie Presley
1995
Dapper romantic comedy star arrested after a dalliance with a prostitute
named Divine Brown
Hugh Grant
1994
Former athlete who allegedly killed his ex-wife and Ronald Goldman
O.J. Simpson
1993
Mustachioed actor who got divorced from Loni Anderson
Burt Reynolds
1992
Film director who dumped his longtime partner for her 19 year old daughter
Woody Allen
1991
Children's actor who had a "Big Adventure" after he was arrested for
lewd conduct in a porn theater
Paul Reubens
+2
Level 66
Jun 20, 2015
You accept Herman for Paul Reubens, why not Peewee?
+4
Level ∞
Feb 4, 2017
That will work now
+11
Level 74
Nov 19, 2018
I still find it appalling that he lost his livelihood just for doing what everybody did in porn theatres (before the internet).
+5
Level 82
Dec 22, 2018
Indeed. I first heard of him in such questions I think, went to Wikipedia to check what it's all about and it's completely ridiculous. They could arrest almost the whole porn theatre every time. The worst punishment should be being asked to leave – if the theatre really decided to stop with such practice.
+4
Level 67
Dec 31, 2020
I think the issue is that he's a children's entertainer. It was still stupid though.
+3
Level 82
Jun 20, 2015
I used to love Ally McBeal but I forgot Robert Downey was ever on it.
+2
Level 77
Feb 4, 2017
Flockheart (or was that Flockhart?), Lithgow, Liu... those are the only ones I remember on it.
+2
Level 82
Apr 21, 2017
Lithgow was on it, too?

The big names were Flockhart, Portia di Rossi, Lucy Liu, Courtney Thorne Smith (she was sort of big in TV at the time)... and I think Cristina Ricci showed up in the last season. Probably around the same time as Robert. I don't remember Lithgow at all, though.

+3
Level 77
Dec 6, 2017
Oh I apparently made that up. For some reason I always felt like he was on it.
+2
Level 88
Dec 22, 2018
Robert Downey actually did prison sentences for drugs, rare for a well known actor.
+3
Level 74
Nov 17, 2019
He had many chances before they finally gave him prison. Lohan is the only one who's had as many chances and I think (I could be wrong) that she did a little time or was booked to but got out of it somehow. Whatever the case, she should have done a few months.
+5
Level 71
Dec 31, 2020
But the good news is he's doing well now! He's been sober since 2003.
+4
Level 61
Dec 20, 2021
Interestingly enough, Mel Gibson was one of the only people to stand by Downey Jr when he was in hot water and he credits him with "keeping food on his table" by offering him a role in a movie when no one else would hire him. And years later, Downey Jr did the same when Gibson was being criticized for making the Passion of the Christ and later going on his drunken anti-Semitic rant.

I find that kind of loyalty and forgiveness inspiring.

+1
Level 69
Dec 19, 2022
Me too.
+5
Level 71
Feb 7, 2017
And to think so many people look up to these celebrities.
+7
Level 88
Dec 19, 2021
And to think so many people who have family, friends and selves who've done dumb sh.

Maybe it's more convenient to judge from a distance.

+1
Level 79
Dec 10, 2023
Maybe it's more convenient not to do dumb sh in the first place. If I had family or friends doing a lot of the stuff on this list I'd be more compassionate, sure, but they'd still get judged pretty harshly.
+4
Level 74
Apr 21, 2017
Worst quiz ever.
+25
Level 54
Apr 21, 2017
Why? The questions are phrased well, the structure is simple but well thought out, and the answers are neither too specific nor too obvious.
+1
Level 51
Apr 21, 2017
Missed Grant, Reynolds, Downey Jr., Givens, and Albert but i was born in 94 so those were all in my childhood or before I was born
+2
Level 82
Jan 8, 2020
was Robin Givens on here before? For marrying or getting beat up by Mike Tyson I presume?
+2
Level 82
Jan 8, 2020
I only missed Agassi's wife. Had no idea the pair were married.
+1
Level 69
Apr 21, 2017
I feel sad for Michael Jackson, not for Albert.
+6
Level 89
Apr 21, 2017
Yeah, poor MJ. He has a short marriage to Elvis's daughter, and six years later proves to be a terrible parent.
+5
Level 66
Apr 21, 2017
Only 10/29 and proud of it.
+18
Level 56
Apr 25, 2017
Yaaay, not knowing things. I also believe that knowledge is dumb.
+11
Level 59
May 6, 2018
Not all knowledge is worth knowing, and all information isn't knowledge either. Got 28/30 and would prefer to have Russian verbs in my brain instead of this crap. But yeah, I must admit these are a lot of fun to do ;)
+1
Level 79
Dec 10, 2023
I hate it when people comment about being proud of low scores but I got 6 and couldn't care less. This knowledge is useless crap about the dramatic and tragic lives of rich people that for some reason we collectively feel the need to spectate all the time.
+4
Level 67
Dec 31, 2020
I got them all except Robert Downey Jr., which is ironic because he's the person I like best of all the ones on this list, and by a fair margin. I didn't know he was on Ally McBeal.
+6
Level 67
Dec 31, 2020
Winona is also pretty great.
+2
Level 73
Dec 31, 2020
I'm proud to say I only knew one answer. (I should have remembered the two -steins though. Apart from that, which in my opinion isn't gossip, I think my life is a lot better not knowing about celebrity gossip.)
+8
Level 88
Dec 20, 2021
Even if it's a subject one has no interest in it's still ridiculous to declare pride in one's ignorance.
+2
Level 77
Dec 25, 2021
Some of these are not gossip at all. Gossip usually is blather about people that isn’t confirmed as true or false, but spread because it’s salacious. These facts are as reliable as facts about historical or political figures. You just don’t like that the quiz is about popular entertainers.
+2
Level 79
Dec 19, 2022
Comments like this are always cringy and give the opposite impression of the commenter than is intended. It doesn't make you sound smarter or better than others...it just makes you sound like you're an oblivious person who lives under a rock lol
+1
Level 79
Dec 10, 2023
I don't understand the flack that people get for saying this. Everybody is ignorant with regard to most things in the universe, so I see no problem in prioritizing certain kinds of knowledge over others. If they want to be proud of it, who cares? Live and let live. I'd much rather come across as an oblivious person who lives under a rock lol than as somebody who gives a crap about any of these stories. Shockingly, people like different things.
+3
Level 79
Dec 31, 2020
Disappointed that I only got 12/30. But I guess pretty good for a Malaysian living in China.
+3
Level 59
Jan 1, 2021
hey, im american and i got 4
+4
Level 15
Dec 31, 2020
Mustachioed actor? Tom Selleck!
+3
Level 74
Dec 19, 2022
When that's the clue, you have two primary choices - Selleck or Reynolds. Then you read the rest or just go with trial-and-error.
+3
Level 66
Dec 31, 2020
I have never heard of Aiken, Vick or Albert. Perhaps the quiz description should make it clear that some of these people are only 'famous' in their local area.
+5
Level 95
Dec 19, 2021
The quiz is called US Celebrity gossip.
+2
Level 82
Nov 30, 2023
Too US-centric apparently
+2
Level 68
Dec 21, 2021
Only got 15 first try, probably too young and too non-american to score higher. Pretty disappointed at not getting Charlie Sheen and Woody Allen though!
+3
Level 65
Dec 19, 2022
I feel like you could accept other spellings for Presley
+1
Level 79
Dec 10, 2023
Like what!?
+2
Level 51
Dec 19, 2022
1:06 left .. I know too much celebrity gossip
+2
Level 80
Dec 19, 2022
What a simpler time 2001 was, when getting caught shoplifting was considered a scandal
+2
Level 76
Dec 19, 2022
Why not today? Do you know many shoplifting celebrities that don't make that kind of headline anymore after the fact?
+4
Level 82
Dec 19, 2022
I think the standards for sticky-fingered celebrities are largely the same.

The bar has been lowered substantially for presidents and Nazis.

+1
Level 76
Dec 19, 2022
Oh, how I hate missing easy answers because I've jumped questions a few times!
+1
Level 53
Dec 19, 2022
5/32 :D
+6
Level 92
Nov 30, 2023
In the 1996 clue it should be woman not women.
+1
Level 71
Nov 30, 2023
that's what I came here to say
+1
Level ∞
Nov 30, 2023
Fixed