We are now in the middle of Music Awards Season! With the Grammys last month, the iHeartRadio Music Awards just yesterday (March 17, 2025), and the highly anticipated return of the American Music Awards in May, it’s the perfect time to take a nostalgic look back at award shows of the 90s. The 90s were a golden era for music award shows, where the biggest artists of the decade took center stage, sometimes delivering iconic performances and other times making headlines for all the wrong reasons.
From the MTV Video Music Awards (VMAs) to the Grammy Awards and the Billboard Music Awards, the 90s music scene was full of unforgettable moments. Let’s take a deep dive into the best hosts, winners, fashion highs and lows, and the drama that kept us all talking!
Memorable Hosts
Award show hosts in the 90s were often just as entertaining as the performances. Some of the best included:
• 1995 MTV VMAs – Dennis Miller: The comedian’s sarcastic wit wasn’t for everyone, but he kept the night moving.
• 1997 MTV VMAs – Chris Rock: Rock’s sharp humor made this one of the most entertaining VMAs of the decade.
• 1998 Billboard Music Awards – Kathy Griffin: Known for her fearless humor, Griffin kept things fun and unpredictable.
• 1999 Grammys – Rosie O’Donnell: Rosie’s comedic energy kept the ceremony lighthearted in a year filled with strong musical moments.
While some hosts were praised, others were forgettable or misfired with awkward jokes (looking at you, Dennis Miller).
Biggest Winners of the Decade
Some artists absolutely dominated the 90s award shows. Here are a few of the biggest winners:
• Whitney Houston – Her Bodyguard soundtrack swept the 1994 Grammys, including Album of the Year.
• Mariah Carey & Boyz II Men – “One Sweet Day” ruled the Billboard Music Awards in 1996.
• TLC – Took home multiple awards in the late 90s, especially after CrazySexyCool.
• Nirvana – Won Best Alternative Video at the 1992 VMAs for “Smells Like Teen Spirit.”
• Madonna – Continued her reign, winning Video of the Year in 1998 for “Ray of Light.”
• Will Smith – Scored several awards in the late 90s for his switch from hip-hop to blockbuster solo rap.
Best & Worst Dressed
Best Dressed:
• Jennifer Lopez (1999 Grammys) – Before her famous green Versace dress in 2000, J.Lo was already turning heads with glamorous looks.
• Gwen Stefani (1998 VMAs) – Her blue hair and bindi made her one of the most memorable fashion icons of the decade.
• TLC (1995 VMAs) – Their matching futuristic outfits were both bold and trendsetting.
• Mariah Carey (1997 Billboard Awards) – Elegant and effortlessly stylish in a black mini-dress.
Worst Dressed:
• Rose McGowan (1998 VMAs) – The infamous barely-there chain dress stole headlines for all the wrong reasons.
• Marilyn Manson (1997 VMAs) – While Manson’s aesthetic was part of his appeal, his bizarre, gothic ensembles didn’t always translate well on the red carpet.
• Britney Spears (1999 American Music Awards) – The all-white lace outfit was more prom night than pop star.
Biggest Award Show Drama
It wouldn’t be a 90s award show without a little controversy! Some of the most unforgettable moments included:
• 1991 MTV VMAs: Pee-Wee Herman’s Surprise Return – After his real-life scandal, Pee-Wee opened the show with “Heard any good jokes lately?” The audience erupted in laughter.
• 1992 VMAs: Nirvana vs. Guns N’ Roses – A near brawl between Nirvana’s Krist Novoselic and Axl Rose nearly stole the show.
• 1994 VMAs: Michael Jackson & Lisa Marie Presley’s Kiss – Their awkward on-stage kiss had the world wondering just how real their relationship was.
• 1995 Source Awards: East Coast vs. West Coast Tension – Suge Knight’s infamous speech calling out Puff Daddy escalated the East Coast-West Coast feud.
• 1997 VMAs: Fiona Apple’s Speech – Instead of thanking her team, Apple delivered a rant against the industry, famously saying, “This world is bulls***.”
• 1999 MTV VMAs: Lil’ Kim’s Infamous Outfit – The purple pasty ensemble became one of the most talked-about fashion moments ever.
Final Thoughts
The 90s award shows weren’t just about handing out trophies—they were full of iconic performances, wild fashion, and unforgettable drama. Whether it was the spectacle of Britney Spears and NSYNC taking the stage, the raw energy of Nirvana, or the unpredictable moments of live TV, the 90s gave us some of the best pop culture moments in music history.
What’s your favorite 90s award show moment? Let us know in the comments!
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Written by station manager, producer, host and jack of all 90s Plus Radio trades – RichJams. I host RichJams Live on Sat. at 2 pm ET.
