Category of Bosses
Boss's Category
70s
80s-90s
2000s-
100

This character, played by Steve Carell on the American version of The Office, managed the Dunder Mifflin Scranton branch and famously declared "I declare bankruptcy!"

Michael Scott

100

This phrase is used to compliment someone who's killing it.

What is "like a boss"?

100

What was the highest grossing movie of the 70's? Jaws Star Wars The Godfather

What is Star Wars

100

This 80's rocker was know for biting the head off of a live bat during a concert.

Who is Ozzy Osbourne?

100

It was cool to make up "facts" about this martial arts star.

Who is Chuck Norris?

200

As the co-founder and former CEO of Apple, this tech visionary was known for his demanding management style and iconic black turtleneck.

Steve Jobs

200

This rock icon, known for hits like Born to Run and Dancing in the Dark, has long been nicknamed "The Boss."

Who is Bruce Springsteen?

200

Which film told us to stay out of the water and had the famous quote, "We're going to need a bigger boat?"

Jaws

200

Who is know for this famous quote, "I pity the fool."

Who is Mr T?

200

Foam footwear, open in the back

What is Croc?

300

This Springfield nuclear power plant owner is known for his sinister grin and iconic catchphrase: "Excellent."

Who is Mr. Burns?

300

In gaming, this type of enemy is usually found at the end of a level and is tougher than regular foes.

What is a boss fight?

300

Who sang the 1978 hit, YMCA? The Village Idiots The Angry Villagers The Village People

What is The Village People

300

The product Michael Jackson was advertising when he was set on fire.

What is Pepsi?

300

Instead of skating, skateboarding, scooting or biking, children used these shoes on wheels.

Heelys

400

This cranky boss of the Krusty Krab is always yelling “Money!” and paying SpongeBob minimum wage.

Who is Mr. Krabs?

400

This term refers to someone who’s both stylish and successful—often used to describe confident, empowered women in leadership.

What is a girlboss?

400

TV's longest running game show was launched in 1972 and it still runs every day. What show is it?

The Price Is Right

400

In 'Aladdin' (1992), this actor voiced The Genie?

Who is Robin Williams?

400

The first winner of the Academy Award for Best Animated Feature in 2001

What is Shrek.

500

a German designer fashion company headquartered in Metzingen, Baden-Württemberg, Germany

Hugo Boss

500

This 2011 film stars Jason Bateman, Charlie Day, and Jason Sudeikis as employees plotting revenge on their terrible employers.

What is Horrible Bosses?

500

One of the most famous educational computer games of all times was launched in 1971 which features a group of people traveling West, with many often dying of dysentery?

What is the Oregon Trail

500

This style of clothing/genre of music was made popular by the Seattle-based band Nirvana.

What is grunge?

500

The first adult animated show that follows a family that doesn't hate each other, own their own business, and are still broke. And also sing original songs. 

What is Bob's Burgers?