Celebrity Gossip by Year

Guess these mostly-American celebrities who were the subject of a major piece of celebrity gossip.
Quiz by Quizmaster
Last updated: December 27, 2019
First submittedNovember 28, 2014
Times taken15,944
Enter answer here
 / 30 guessed
The quiz is paused. You have remaining.
You scored / = %
This beats or equals % of test takers also scored 100%
The average score is
Your high score is
Your fastest time is
Keep scrolling down for answers and more stats ...
This sex criminal with ties to Prince Andrew and Bill Clinton commits suicide
in his jail cell - or does he?
Jeffrey Epstein
This singer marries American model Hailey Baldwin
Justin Bieber
This powerful Hollywood producer is the first of many celebrities
to be fired for sexual harassment
Harvey Weinstein
This actress files for divorce and asks for full custody of children
Shiloh, Maddox, Vivienne, Knox, Zahara, and Pax
Angelina Jolie
This former decathlete changes gender
Caitlyn Jenner
This over-exposed reality star threatens to "break the internet" by
releasing nude photos
Kim Kardashian
This naughty singer twerks at the Video Music awards
Miley Cyrus
This actress is caught cheating on boyfriend and costar Robert Pattinson
Kristen Stewart
In a famous meltdown, this actor claims to be a "warlock" with "tiger blood"
Charlie Sheen
After numerous affairs are revealed, this athlete is divorced by
Swedish model Elin Nordegren
Tiger Woods
In a shocking act of villainy, Kanye West interrupts this singer's acceptance
speech at an awards show
Taylor Swift
This "American Idol" runner-up surprises the world by announcing that he is gay
Clay Aiken
This football player is sentenced to prison for running a dog-fighting ring
Michael Vick
This actor blames Jews for all the world's problems after being arrested for DUI
Mel Gibson
This actor jumps on Oprah's couch to declare his love
Tom Cruise
Britney Spears becomes engaged to this disheveled backup dancer
Kevin Federline
This heiress becomes famous for being famous - and also for a sex tape
Paris Hilton
This singer dangles his newborn baby from a hotel balcony
Michael Jackson
This "Beetlejuice" star is arrested for shoplifting
Winona Ryder
While starring in "Ally McBeal", this critically-acclaimed actor is arrested for
cocaine and valium possession
Robert Downey Jr.
This actress gets divorced from tennis star Andre Agassi
Brooke Shields
Bill Clinton says he did not have sexual relations with this woman,
but later admits that he did
Monica Lewinsky
This basketball announcer bites a woman
Marv Albert
Michael Jackson's brief marriage to this woman comes to an end
Lisa Marie Presley
This dapper romantic comedy star is arrested after a dalliance with a prostitute
named Divine Brown
Hugh Grant
This former athlete allegedly kills his ex-wife and Ronald Goldman
O.J. Simpson
Actress Loni Anderson and this mustachioed actor get divorced
Burt Reynolds
This film director dumps his longtime partner for her 19 year old daughter
Woody Allen
This children's actor has a "Big Adventure" after he is arrested for
lewd conduct in a porn theater
Paul Reubens
This billionaire and his wife Ivana begin divorce proceedings
Donald Trump
Level 78
Dec 2, 2014
I can't sense the sarcasm with the Clay Aiken question...
Level 55
Jun 20, 2015
nobody was surprised at the content of his announcement, just that he felt the need to make an announcement.
Level 75
Dec 8, 2017
It's also ironic because no one knows him outside of the US
Level 71
Nov 17, 2019
No one cares about him IN the US.
Level 67
Jun 20, 2015
You accept Herman for Paul Reubens, why not Peewee?
Level ∞
Feb 4, 2017
That will work now
Level 76
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).
Level 76
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.
Level 79
Jun 20, 2015
I used to love Ally McBeal but I forgot Robert Downey was ever on it.
Level 83
Feb 4, 2017
Flockheart (or was that Flockhart?), Lithgow, Liu... those are the only ones I remember on it.
Level 79
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.
Level 83
Dec 6, 2017
Oh I apparently made that up. For some reason I always felt like he was on it.
Level 80
Dec 22, 2018
Robert Downey actually did prison sentences for drugs, rare for a well known actor.
Level 71
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.
Level 71
Feb 7, 2017
And to think so many people look up to these celebrities.
Level 76
Apr 24, 2017
My thoughts exactly.
Level 66
Apr 21, 2017
Worst quiz ever.
Level 55
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.
Level 44
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
Level 79
Jan 8, 2020
was Robin Givens on here before? For marrying or getting beat up by Mike Tyson I presume?
Level 79
Jan 8, 2020
I only missed Agassi's wife. Had no idea the pair were married.
Level 60
Apr 21, 2017
I feel sad for Michael Jackson, not for Albert.
Level 82
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.
Level 64
Apr 21, 2017
Only 10/29 and proud of it.
Level 54
Apr 25, 2017
Yaaay, not knowing things. I also believe that knowledge is dumb.
Level 62
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 ;)
Level 68
Dec 8, 2017
A few these are quite American specific. The 2007 and 1997 answers are complete unknowns in Britain, their escapades didn't make the news over here. The 2008 answer may be the same, but I don't watch any of those programs so it could just be I missed it.
Level 71
Nov 17, 2019
I'm in the US and those were the only ones I got wrong.
Level 75
Dec 22, 2018
Justin Bieber is married? Poor woman.
Level 74
Apr 27, 2019
missed 2 and both were recent ones...2018 and 2016
Level 78
Nov 8, 2019
* Alleged billionaire