Superbowl Halftimes
Billboard
Grammy
Music 3
Music 4
100

Perhaps the most infamous half time show of all time headlined these two musicians, one of which had a wardrobe malfunction

Janet Jackson & Justin Timberlake

100

Most overall Hot 100 songs

Drake (331)

100

This powerhouse couple has a total of 60 grammys between the two of them, one of which is the most awarded of all-time

Beyonce & Jay-Z

100

When did Beyoncé win the Grammy for Best Album of the Year for the first time?

2025

100

Which one-named singer, known as the Princess of R&B, tragically died in a plane crash in 2001?

Aaliyah

200

Who performed at the most-viewed halftime show

Rihanna

200

Longest run at #1 on Hot 100

Old Town Road

200

Which Marvel soundtrack won two grammys

Black Panther

200

What is the most decorated rap song in Grammy Awards history?

Kendrick Lamar's "Not Like Us"

200

What English rockstar wrote the soundtrack for Tarzan (1999)?

Phil Collins

300

In 1993, this artist's performance got more views than the game itself, this marked the first time this has happened

Michael Jackson

300

What singer has had a Billboard No. 1 hit in each of the last four decades?

Mariah Carey

300

Who won record of the year in 2020 and 2021

Billie Ellish

300

What artists recorded two of their bestselling albums while they were behind bars?

Johnny Cash

300

In what song does Megan Thee Stallion rap, "Gobble me, swallow me, drip down the side of me / Quick, jump out 'fore you let it get inside of me"?

WAP

400

In 2016 this artist performed at the halftime show, becoming one of seven to ever perform more than once for the Superbowl

Bruno Mars

400

Who is the only country artist to have a Top 20 hit on the Billboard Hot Country Songs chart for six straight decades?

Dolly Parton

400

Why does it have the name "Grammy"

The material its made of. The Grammy is made from a secret zinc alloy called "Grammium" and plated with 24-karat gold

400

Which singer was the only solo musician to have a #1 hit in every year of the 1990s?

Mariah Carey

400

What is the best-selling album of all time?

Thriller - Michael Jackson

500

In 1989, the headliners were a magician and a celebrity impersonator. Which celebrity was impersonated

Elvis Presley

500

This wandering color band made a satirical song that mocked how popular music doesn't have to have a purpose, it just has to be catchy that topped at spot 23 on the US Billboard 100

"It's the _ that brings you back"

Blues Traveler - Hook

500

Who is the only person to refuse a grammy

Sinead O' Connor

500

Who is the only performer to ever turn down Weird Al's request to parody their music?

Prince

500

Lana Del Rey's husband name

Jeremy Dufrene

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