175 Tricky 90s Music Trivia: How Well Do You Know the Hits

James Edwards

April 9, 2025Remember the first time you heard “Smells Like Teen Spirit”? The 90s music scene changed everything. We went from hair metal to grunge, R&B to boy bands, and hip-hop became mainstream.
But these days, it’s hard to recall all those songs that once filled our Walkman headphones and car stereos.
Maybe you think you know ’90s music. You recognize Britney’s “…Baby One More Time” the second it plays. You can still rap every word to “Ice Ice Baby.” But can you name TLC’s biggest hit? Or remember which Spice Girl left the group first?
This trivia challenge will test your ’90s music knowledge – from one-hit wonders to chart-topping albums. Let’s see if your memory is as good as you think!

Why ’90s Music Trivia Is a Fun Party Activity

’90s music trivia brings life to any party by tapping into our shared memories of an amazing musical decade. When you play this game with friends, it creates an instant connection through songs everyone knows and loves.
The ’90s gave us so many different music styles – from grunge and hip-hop to boy bands and pop divas. This variety means there’s something for every guest at your party to get excited about.
Music trivia also works for all types of parties. It can break the ice at gatherings where not everyone knows each other, and it adds friendly competition to events with close friends.
What makes ’90s trivia especially fun is how it brings back personal memories. Each song might remind someone of their first dance, a summer road trip, or hanging out with friends after school.
Plus, it’s super easy to set up! You just need some basic questions about ’90s artists, songs, and music videos.

General 90s Music Trivia to Test Your Knowledge

Which boy band released the hit song “I Want It That Way” in 1999?Backstreet Boys

What was the title of Britney Spears’ debut single released in 1998?…Baby One More Time

Which iconic rapper was tragically killed in 1996 in a drive-by shooting in Las Vegas?Tupac Shakur

What 1991 single by R.E.M. begins with the lyrics “That’s great, it starts with an earthquake…”?It’s the End of the World as We Know It (And I Feel Fine)

Who was the lead singer of the band No Doubt during their 90s rise to fame?Gwen Stefani

Which 1994 song by TLC warned listeners not to go chasing waterfalls?Waterfalls

Which group is known for the 1995 hit “Gangsta’s Paradise”?Coolio featuring L.V.

What album did Alanis Morissette release in 1995 that featured the hit “You Oughta Know”?Jagged Little Pill

Which UK girl group had a 1996 hit with “Wannabe”?Spice Girls

Which 90s pop duo had a hit with “MMMBop”?Hanson

Which famous Canadian singer had a massive hit with “My Heart Will Go On” in 1997?Celine Dion

Which 90s hip-hop group is known for the song “No Diggity”?Blackstreet

Which artist released the hit “Vogue” in 1990?Madonna

Which band’s 1991 album “Ten” became one of the defining records of the grunge movement?Pearl Jam

Which electronic dance anthem by Darude was released in 1999?Sandstorm

Which rock band scored a 1997 hit with the song “Semi-Charmed Life”?Third Eye Blind

What was the debut single of Destiny’s Child in the late ’90s?No, No, No

Which 90s band featured sisters Carnie and Wendy Wilson?Wilson Phillips

Which Latin pop artist had a breakout English-language hit with “If You Had My Love” in 1999?Jennifer Lopez

Which 1992 single by Sir Mix-a-Lot begins with the line “I like big butts and I cannot lie”?Baby Got Back

Which Seattle-based band released “Black Hole Sun” in 1994?Soundgarden

Which boy band featured Justin Timberlake and released “Tearin’ Up My Heart” in the 90s?*NSYNC

Which 90s female artist had a hit with “You’re Still the One” in 1998?Shania Twain

What was the debut album of Lauryn Hill released in 1998?The Miseducation of Lauryn Hill

Which song did Natalie Imbruglia release in 1997 that became a worldwide hit?Torn

Which rap duo released the 1994 hit “Regulate”?Warren G and Nate Dogg

Which band released the hit “Iris” in 1998 for the “City of Angels” soundtrack?Goo Goo Dolls

Who sang the 1995 chart-topper “Kiss from a Rose”?Seal

Which American rock band released “Smells Like Teen Spirit”?Nirvana

Which late 90s song by Eiffel 65 had lyrics about a blue world?Blue (Da Ba Dee)

Which 90s R&B group was known for the song “End of the Road”?Boyz II Men

Which Irish singer had a 1990 hit with “Nothing Compares 2 U”?Sinéad O’Connor

Which hit by MC Hammer became synonymous with parachute pants in the 90s?U Can’t Touch This

Which female trio released the empowering anthem “No Scrubs” in 1999?TLC

Which hit 1996 song by Los Del Rio sparked a global dance craze?Macarena

Pop Icons Ft. 90s Music Trivia

Which pop icon released the album “Ray of Light” in 1998, marking a major reinvention of her sound?Madonna

Which former Mouseketeer burst onto the pop scene with “…Baby One More Time” in 1998?Britney Spears

Which boy band featured lead vocals from Nick Carter and rose to fame with hits like “As Long As You Love Me”?Backstreet Boys

Which pop diva had her first number one hit with “Vision of Love” in 1990?Mariah Carey

Which pop artist’s 1999 single “Genie in a Bottle” became a worldwide sensation?Christina Aguilera

Which pop star began her solo career in the late 90s after success with the group Destiny’s Child?Beyoncé

Which Latin heartthrob became an international star with the 1999 hit “Livin’ la Vida Loca”?Ricky Martin

Which ‘90s pop icon was known for her hits “That’s The Way Love Goes” and “Together Again”?Janet Jackson

Which male pop star released the album “My Way” in 1997, featuring the hit “You Make Me Wanna”?Usher

Which Canadian pop-rock star first gained fame in the early 90s with “Let’s Talk About Love”?Celine Dion

Which teen pop group, featuring Justin Timberlake, released “I Want You Back” in 1996 in Germany?*NSYNC

Which British pop group sold over 80 million records worldwide and popularized the phrase “Girl Power”?Spice Girls

Which singer had a major hit with “I’m Your Angel” alongside Celine Dion in 1998?R. Kelly

Which female artist released the hit “Come On Over Baby (All I Want Is You)” in 1999?Christina Aguilera

Which pop icon’s 1990 song “Vogue” paid tribute to Hollywood’s golden era?Madonna

Which American boy band released the hit “Summer Girls” in 1999?LFO

Which 90s pop star was known for the hits “If You Had My Love” and “Waiting for Tonight”?Jennifer Lopez

Which singer-songwriter released the heartfelt ballad “Angel” in 1998?Sarah McLachlan

Which 90s pop singer had hits with “Crush” and “I Wanna Be with You”?Mandy Moore

Which solo artist was part of the duo Wham! Before launching a huge solo career, with 90s hits like “Fastlove”?George Michael

Which pop icon was known for her unique voice and the 1991 hit “From a Distance”?Bette Midler

Which 90s singer was known for the hit single “Bitch” in 1997?Meredith Brooks

Which pop group had a hit with “Truly Madly Deeply” in 1997?Savage Garden

Which pop icon was featured on the 1995 hit “Scream” alongside her brother?Janet Jackson

Which Latin pop singer rose to fame with the hit “Dreaming of You” before her tragic death in 1995?Selena

Which 90s teen sensation sang the hit “Candy” in 1999?Jessica Simpson

Which pop singer released “You Oughta Know” and became a voice for 90s female angst?Alanis Morissette

Which male artist was known for the 1999 hit “Back at One”?Brian McKnight

Which female group released the hit “I’m So Into You” in 1993?SWV (Sisters With Voices)

Which 90s star gained fame with the hit “This Is How We Do It” in 1995?Montell Jordan

Which pop diva’s 1993 ballad “Hero” became an anthem of hope and empowerment?Mariah Carey

Which 90s group consisted of four brothers and released the hit “The Hardest Thing”?98 Degrees

Which singer had a massive 1990 hit with “Nothing Compares 2 U”?Sinéad O’Connor

Which 90s pop act was known for their harmonies in the hit “I Swear”?All-4-One

Which artist sang the 1998 smash “Together Again” to honor friends lost to AIDS?Janet Jackson

Rock Music Hits of 90s

Which Seattle band released the 1991 grunge anthem “Smells Like Teen Spirit”?Nirvana

Which alternative rock band had a hit with “1979” in 1996?The Smashing Pumpkins

Which band’s debut album “Core” included the hit “Plush”?Stone Temple Pilots

Which Irish rock band released “One” in 1991, featured on their album Achtung Baby?U2

Which British band had a 1997 hit with “Bittersweet Symphony”?The Verve

Which alternative rock group released “Loser” in 1994, launching them into stardom?Beck

Which band fronted by Gwen Stefani had a hit with “Just a Girl” in 1995?No Doubt

Which American rock band released “Under the Bridge” in 1992?Red Hot Chili Peppers

Which song by Radiohead features the line “I’m a creep, I’m a weirdo”?Creep

Which band’s 1995 hit “Name” was their breakthrough before “Iris” made them global stars?Goo Goo Dolls

Which Seattle-based band released the song “Jeremy” in 1992?Pearl Jam

Which alternative rock duo had a hit with “Possum Kingdom” in 1994?Toadies

Which band’s 1997 hit “Tubthumping” included the lyrics “I get knocked down, but I get up again”?Chumbawamba

Which song by Blind Melon is best known for its music video featuring a girl in a bee costume?No Rain

Which American band had a 1994 alternative hit with “Shine”?Collective Soul

Which song did Soundgarden release in 1994 that became one of their most iconic tracks?Black Hole Sun

Which band had hits in the 90s with “Inside Out” and “How’s It Going to Be”?Third Eye Blind

Which 90s group released the song “She Don’t Use Jelly”?The Flaming Lips

Which English band released “Song 2” in 1997, known for its iconic “Woo-hoo” chorus?Blur

Which ’90s female-fronted band had a major hit with “Seether”?Veruca Salt

Which grunge band released the song “Would?” for the Singles soundtrack?Alice in Chains

Which American band had a hit with “Two Princes” in 1993?Spin Doctors

Which band’s song “Good” was a breakout alternative hit in 1995?Better Than Ezra

Which 90s group released “What’s the Frequency, Kenneth?” in 1994?R.E.M.

Which band is known for the 1996 rock song “Pepper”?Butthole Surfers

Which alternative rock band released the song “Santa Monica” in 1995?Everclear

Which Canadian rock band had a hit with “One Week” in 1998?Barenaked Ladies

Which post-grunge band released the 1997 single “Freshmen”?The Verve Pipe

Which American band released “All Star” in 1999, also known for the Shrek soundtrack?Smash Mouth

Which ska-punk band had a 1997 hit with “Sell Out”?Reel Big Fish

Which 90s alternative band had a hit with “Sex and Candy”?Marcy Playground

Which rock band is known for the 1995 hit “Breakfast at Tiffany’s”?Deep Blue Something

Which punk rock band released “When I Come Around” in 1995?Green Day

Which 90s band had a hit with “Flagpole Sitta” in 1997?Harvey Danger

Which female-led rock band released “Stay (I Missed You)” in 1994?Lisa Loeb & Nine Stories

90s Music Trivia: Hip-Hop Classics

Which 1992 track by Sir Mix-a-Lot became a pop culture phenomenon for its love of curves?Baby Got Back

Which R&B group released the emotional ballad “End of the Road” in 1992?Boyz II Men

Which rapper had a breakout hit in 1990 with “Ice Ice Baby”?Vanilla Ice

Which 1996 hit by Blackstreet featured Dr. Dre and Queen Pen?No Diggity

Which 1995 TLC song warned about avoiding scrubs who “hang out the passenger side of their best friend’s ride”?No Scrubs

Which hip-hop duo released the 1994 classic “Regulate”?Warren G and Nate Dogg

Which R&B singer released the debut album What’s the 411? in 1992?Mary J. Blige

Which 1993 track by Snoop Doggy Dogg featured the lyric “Snoop Doggy Dogg, you need to get a jobby job”?Who Am I? (What’s My Name?)

Which 1997 Puff Daddy song was a tribute to The Notorious B.I.G.?I’ll Be Missing You

Which rap group asked “Can’t nobody hold me down” in their 1997 single?Puff Daddy featuring Mase

Which female rapper rose to fame with the 1997 hit “The Rain (Supa Dupa Fly)”?Missy Elliott

Which West Coast rapper released The Chronic in 1992?Dr. Dre

Which 1994 hit by Aaliyah was produced by R. Kelly and sampled the Isley Brothers?Back & Forth

Which rap group had a massive hit with “Jump” in 1992 while still in their early teens?Kris Kross

Which 1999 single by Destiny’s Child marked their rise to mainstream R&B fame?Bills, Bills, Bills

Which duo had a crossover R&B/hip-hop hit with “This Is How We Do It” in 1995?Montell Jordan

Which 1996 song by Bone Thugs-N-Harmony was a tribute to their deceased mentor Eazy-E?Tha Crossroads

Which 1998 Lauryn Hill song featured the chorus “You might win some, but you just lost one”?Lost Ones

Which rapper’s 1994 debut album, Ready to Die, became a hip-hop classic?The Notorious B.I.G.

Which 1991 Naughty by Nature hit begins with “Hip hop hooray, ho, hey, ho”?Hip Hop Hooray

Which R&B artist released “Pony” in 1996, becoming a staple of ’90s slow jams?Ginuwine

Which 1996 Missy Elliott–penned song was a hit for 702?Steelo

Which rapper warned, “Don’t push me ’cause I’m close to the edge” in a song revived in the 90s by Nas and Puff Daddy?Grandmaster Flash (Revived in 1997 as The Message sample)

Which duo released “Creep” in 1994, continuing their streak of sultry R&B hits?TLC

Which artist is known for the 1995 R&B hit “You Used to Love Me”?Faith Evans

Which East Coast rapper famously feuded with Tupac Shakur in the 90s?The Notorious B.I.G.

Which 1995 2Pac hit featured a sample of The Five Stairsteps’ “O-o-h Child”?Keep Ya Head Up

Which 1998 R&B hit by Brandy and Monica became a chart-topping duet?The Boy Is Mine

Which 90s rap duo was known for wearing backward pants and high-energy performances?Kris Kross

Which rapper known for “Hot Spot” and “Crush on You” rose to fame with Junior M.A.F.I.A.?Lil’ Kim

Which OutKast track from 1996 put Southern hip-hop on the map?Elevators (Me & You)

Which 1991 song by DJ Jazzy Jeff & The Fresh Prince celebrated summer?Summertime

Which female R&B group had hits like “Weak” and “Right Here (Human Nature Remix)”?SWV (Sisters With Voices)

Which 1993 song by Tag Team became a sports arena staple?Whoomp! (There It Is)

Which rapper known for “Nuthin’ But a ‘G’ Thang” also helped launch Eminem’s career?Dr. Dre

One-Hit Wonder 90s music trivia

Which 1996 hit by Los Del Rio became a global dance sensation?Macarena

Which 1997 song by Natalie Imbruglia, originally written by Ednaswap, became her breakout hit?Torn

Which 1995 hit by White Town featured a blend of electronic beats and vintage samples?Your Woman

Which band is known for their 1995 hit “Breakfast at Tiffany’s”?Deep Blue Something

Which 1993 anthem by Tag Team remains a sports arena favorite?Whoomp! (There It Is)

Which 1995 R&B hit by Dionne Farris was her only major solo success?I Know

Which New Zealand group scored a one-hit wonder with “How Bizarre” in 1996?OMC

Which Danish-Norwegian pop group went viral with their 1997 hit “Barbie Girl”?Aqua

Which 1997 hit by Meredith Brooks became a feminist anthem?Bitch

Which French house act had a 1998 hit with “Music Sounds Better with You”?Stardust

Which 1997 alt-rock track by Marcy Playground was known for its dreamy, moody tone?Sex and Candy

Which 1998 hit by New Radicals included the line “You get what you give”?You Get What You Give

Which 1990 ballad by Sinéad O’Connor was originally written by Prince?Nothing Compares 2.

Which 1995 single by Joan Osborne questioned the nature of divinity?One of Us

Which 1993 song by 4 Non Blondes features the shout “What’s going on?”What’s Up?

Which 1995 hit by Blessid Union of Souls contains the line “I believe that love is the answer”?I Believe

Which 1999 spoken-word track by Baz Luhrmann offers life advice to graduates?Everybody’s Free (To Wear Sunscreen)

Which 1999 Latin dance hit by Lou Bega listed women’s names throughout the song?Mambo No. 5

Which 1996 ballad by The Verve Pipe reflected on past regrets and youth?The Freshmen

Which 1993 Eurodance hit by Haddaway repeatedly asks, “What is love?”What Is Love

Which 1991 alt-rock hit by Jesus Jones celebrates living in the moment?Right Here, Right Now

Which 1994 track by Crash Test Dummies is known for its deep vocal tone and quirky lyrics?Mmm Mmm Mmm Mmm

Which 1999 dance track by Eiffel 65 featured a “blue” world and a catchy chorus?Blue (Da Ba Dee)

Which 1990 song by C+C Music Factory became iconic for the line “Everybody dance now”?Gonna Make You Sweat (Everybody Dance Now)

Which 1997 alt-rock song by Chumbawamba declared “I get knocked down, but I get up again”?Tubthumping

Which 1996 track by Primitive Radio Gods was known for its use of a B.B. King sample?Standing Outside a Broken Phone Booth with Money in My Hand

Which 1990 song by Snap! Became famous for the line “I’ve got the power”?The Power

Which 1996 hit by Dishwalla tells the story of a boy asking about God’s appearance?Counting Blue Cars

Which funky 1990 hit by Deee-Lite became known for its psychedelic visuals and catchy beat?Groove Is in the Heart

Which 1991 novelty rap hit by Gerardo mixed English and Spanish lyrics?Rico Suave

Which reggae fusion track by Ini Kamoze became a hit in 1994?Here Comes the Hotstepper

Which 1999 instrumental electronic track by Darude became a club staple?Sandstorm

Which 1997 hit by Ultra Naté became an empowering club anthem?Free

Which 1994 hip-hop hit by Funkdoobiest featured the line “Bow wow wow, yippie yo yippie yay”?The Funkiest

Which 1990 hit by The La’s featured the unforgettable line “There she goes again”?There She Goes

The Bottom Line

Our trip through 90s music shows just how rich and varied this decade was. From Nirvana to the Spice Girls, these songs shaped a generation and still get us singing today.
So what’s the point of all this trivia? It’s about more than just testing your memory. These songs connect us to specific moments in our lives – first crushes, road trips with friends, or dancing in your bedroom with a hairbrush microphone.
The next time you’re with friends, pull out these trivia questions and watch how quickly everyone jumps in. You’ll be amazed at how music brings people together and sparks conversations.
Want more ’90s nostalgia? Check out our other posts about fashion and movies from the decade that gave us so much to remember.

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