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Celebrities in Trouble
Sports of 2010s
1950s
To the 99s
100

What '90s plush toy line includes Flash the Dolphin and Splash the Whale among its original nine characters?

What is Beanie Babies?

100

Who infamously interrupted Taylor Swift's acceptance speech at the 2009 Video Music Awards show saying in part "Beyonce had one of the best videos of all time"?

Who is Kanye West?

100

In a redemption story that spanned the decade, Tiger Woods won which of the four PGA Majors in 2019 to complete his epic comeback in the world of golf?

What is The Masters?

100

Les Paul was a 1950s pioneer of which instrument?

What is Guitar?

100

What hockey "Great One" wore uniform #99 throughout his NHL career with the Oilers, Kings, Blues and Rangers?

Who is Wayne Gretzky?

200

Which 1996 game by Hasbro challenges players with the commands "Twist it!" and "Pull it!" among its three core instructions?

What is Bop It?

200

What singer of the sixties rock band The Doors was arrested for indecent exposure on stage in Miami in 1969?

Who is Jim Morrison?

200

The story of what Notre Dame linebacker's fake girlfriend drew significant media attention and public scrutiny in 2013?

Who is Manti Te'o?

200

Richard Penniman was better known as…?

Who is Little Richard?

200

All rise for this Yankees slugger, who hit62regular season home runs in 2022, while wearing #99.

Who is Aaron Judge?

300

In 1853, who founded the first company to manufacture blue jeans?

What is Levi Strauss?

300

What star of The Parent Trap was taken into custody for possession of cocaine and a DUI in 2007?

Who is Lindsay Lohan?

300

Which MLB team won the World Series in 2016, ending a 108-year championship drought?

Who are the Chicago Cubs?

300

Who is often called The King of Soul?

Who is Sam Cooke?

300

In 2012, what punk band released three albums, with the last of them--Tré, named for their drummer--containing the song 99 Revolutions?

Who is Green Day?

400

"Trail's End" is a specially-made brand of popcorn sold as a fundraiser for what youth organization?

What is Boy Scouts/Boy Scouts of America?

400

In 2014, which Canadian pop star was accused of vandalism for egging a neighbor's house?

Who is Justin Bieber?

400

What horse won the Triple Crown in 2015, an achievement that hadn't been done in 37 years?

What is American Pharoah?

400

Who had a major hit with 'White Christmas'?

Who is Bing Crosby?

400

What band, with a name out of The Wizard of Oz, had a hit in 1979 with 99, a song about a sterile society where love is forbidden?

Who is Toto?

500

A 2004 novel by Jeff Lindsay inspired what Showtime series about a forensic technician moonlighting as a serial killer?

What is Dexter?

500

Which rapper was involved in a street brawl in Stockholm in 2019, leading to his arrest and trial?

Who is A$AP Rocky?

500

Which undefeated boxer extended his record to 50-0 by defeating former UFC champion Conor McGregor in a highly publicized 2017 fight?

Who is Floyd Mayweather?

500

What year did the First Grammy Awards take place?

What is 1959?

500

Since the 19th century, what brand of soap has been advertised with the slogan,"99 and 44/100ths percent pure"?

What is Ivory?

600

What 1992 song by Nirvana is the namesake of the Sirius XM radio channel dedicated to '90s grunge and alternative rock?

What is Lithium?

600

What It's a Man's Man's Man's World singer's various run-ins with the law included car theft, drug offenses and domestic assault?

Who is James Brown?

600

Which New York Yankee player broke the single-season home run record for rookies in 2017?

Who is Aaron Judge?

600

What were the names of Dennis' parents on "Dennis the Menace"?

Who is Henry and Alice?

600

What Emmy award winning comedy series starring Andy Samberg and Terry Crews follows the exploits of Det. Jake Peralta and his colleagues?

What is Brooklyn 99?

800

First published in 1855,Leaves of Grass was a poetry collection by what American poet?

Who is Walt Whitman?

800

What star of Reality Bites was caught shoplifting from Saks Fifth Avenue in 2001, an event that became a significant scandal?

Who is Winona Ryder?

800

Which NHL team won 3 Stanley Cups in the 2010s; in 2010, 2013, and 2015?

Who is Chicago Blackhawks?

800

George Burns was one half of this show; who was the other half?

Who is Gracie Allen?

800

Actress Barbara Feldon played Agent 99 in what '60s spy spoof series, co-created by Mel Brooks?

What is Get Smart?

1000

What former Prime Minister of Pakistan went into self-exile in Dubai in 1998, where she remained head of the Pakistan Peoples Party?

Who is Benazir Bhutto?

1000

What supermodel threw a phone at her maid in 2006, leading to an assault charge?

Who is Naomi Campbell?

1000

In 2013, what Denver Broncos kicker set the record for the longest field goal at 64 yards?

Who is Matt Prater?

1000

What man introduced Kermit the Frog on "Sam and Friends?"

Who is Jim Henson?

1000

What is the proper way to write the number 99 in Roman numerals?

What is XCIX?