- - 27 Vintage Photos from the Grammy Awards — from Michael Jackson's Thrilling Wins to Jennifer Lopez's Internet-Breaking Dress

Stephanie SengweFebruary 1, 2026 at 6:00 AM

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Jennifer Lopez, Michael Jackson, Weird Al Yankovic

Vince Bucci/AFP via Getty; Bettmann Archive/Getty; Ron Galella Collection via Getty

The Grammys are guaranteed to give us something to talk about the next day — or for years to come.

On the red carpet, you won't see any Old Hollywood ballgowns; instead, musicians including Jennifer Lopez and Toni Braxton have taken the opportunity to wear head-snapping gowns that start trends (and make some blush).

And as one of the most visible stages in music, there have been plenty of all-timer performances worth a rewatch, even decades later.

The ceremony, which first took place back in 1959, has also seen a lot of history-making moments from musicians who later became legends, such as Michael Jackson, Beyoncé, Mariah Carey and more.

As we gear up for the 68th Annual Grammy Awards tonight, look back at these vintage photos from shows past.

01 of 27

History Makers

The Jackson 5 and Gladys Knight and the Pips

CBS via Getty

The Jackson Five posed with Gladys Knight and the Pips backstage at the 1974 show after they presented the latter with the Best Rhythm and Blues Vocal Performance by a Duo, Group or Chorus.

02 of 27

The Star Is Here

Barbra Streisand

Bettmann Archive/Getty

A young Barbra Streisand holds up her trophy for her work on A Star Is Born in 1978. "Evergreen (Love Theme from A Star Is Born)" would win the star two of her 10 trophies that night — one for Song of the Year, the other for Best Pop Vocal Performance, Female.

03 of 27

Paying Homage

Annie Lennox & Dave Stewart

Barry King/WireImage

The Eurythmics' Dave Stewart couldn't help but laugh at his bandmate, Annie Lennox, dressed up as Elvis for the 1984 show.

04 of 27

Triple Date

Emmanuel Lewis, Michael Jackson and Brooke Shields

Ron Galella/Ron Galella Collection via Getty

Michael Jackson, who was nominated in 1984 for 12 Grammys for Thriller, arrived with Emmanuel Lewis and Brooke Shields for the history-making night.

05 of 27

The King Is Crowned

Michael Jackson and Quincy Jones

CBS via Getty

They don't call him the King of Pop for nothing: He nearly swept, taking home eight awards that night (a record up to that point) along with producer Quincy Jones.

06 of 27

Oh-So-'80s

Hulk Hogan, Mr. T and Cyndi Lauper

Vinnie Zuffante/Getty

It would be hard to sum up the decade more succinctly than this photo of Hulk Hogan and Mr. T mingling with Cyndi Lauper at the 1985 Grammy Awards.

07 of 27

New on the Scene

Whitney Houston

Ron Galella, Ltd./Ron Galella Collection via Getty

A fresh-faced Whitney Houston held her award for Best Pop Vocal Performance, Female, for the song "Saving All My Love for You" at the 1986 ceremony.

08 of 27

Family Business

Naomi Judd and Wynonna Judd

Jim Smeal/Ron Galella Collection via Getty

Naomi and her daughter Wynonna Judd were a lookalike pair at the same show. The duo won the Best Country Performance by a Duo or Group with Vocal that year.

09 of 27

Cool as a Cucumber

A young Sinead O'Connor opted for a tattoo-inspired biker jacket for the 31st Annual Grammys in 1989.

10 of 27

Breaking Barriers

DJ Jazzy Jeff and Will Smith

Richard Corkery/NY Daily News Archive via Getty

DJ Jazzy Jeff and Will Smith made history at the 1989 Grammys, winning the first-ever trophy for Best Rap Performance for their song "Parents Just Don't Understand."

11 of 27

Unbelievable

Weird Al Yankovic

Ron Galella, Ltd./Ron Galella Collection via Getty

Weird Al Yankovic could hardly believe his eyes as he nabbed an award for Best Concept Music Video in 1989.

12 of 27

Effortless Beauty

Selena Arlene Richie/Getty

Selena was radiant as she posed with her award for Best Mexican-American Album at the 36th Annual Grammys in 1994.

13 of 27

Golden Guys

Boyz II Men

DAN GROSHONG/AFP via Getty

Boyz II Men accented their all-white ensembles with some gold, winning Best R&B Album and Best R&B Performance by a Group in 1995.

14 of 27

All the Wins

Trisha Yearwood

MATT CAMPBELL/AFP via Getty

Trisha Yearwood proudly held her two Grammys — Best Female Country Vocal Performance and Best Country Collaboration with Vocals — in 1998.

15 of 27

For You

Ricky Martin

Vince Bucci/AFP via Getty

Ricky Martin was over the moon as he posed with his Grammy Award for Best Latin Pop Performance for Vuelve.

16 of 27

Hard Launch

Jennifer Lopez

Scott Gries/ImageDirect

Jennifer Lopez made a huge splash at the 2000 show, rocking this risqué Versace gown that legendarily led to the launch of Google Images.

17 of 27

Princess of Pop

Britney Spears

Dave Hogan/Getty

Britney Spears ushered in her era of total domination, performing a medley of "...Baby One More Time" and "From the Bottom of My Broken Heart" in 2000.

18 of 27

Dream Come True

Christina Aguilera

J. Vespa/WireImage

Her fellow Disney alum, Christina Aguilera also snagged her first trophy, winning Best New Artist the same night.

19 of 27

Peek-a-Boo

Toni Braxton

Vinnie Zuffante/Getty

The following year, Toni Braxton rocked a daring ensemble by Richard Tyler to the 2000 ceremony. The R&B singer also won Best Female R&B Vocal Performance for "He Wasn't Man Enough."

20 of 27

Father-Daughter Time

Zoe Kravitz and Lenny Kravitz

Dave Hogan/Getty

Lenny Kravitz was hand-in-hand with daughter Zoë at the 2000 show.

21 of 27

Showing Love

Elton John and Eminem

Dave Hogan/Getty

Sir Elton John and Eminem go in for a hug following their emotional performance of the rapper's song "Stan" in 2001.

22 of 27

True to Self

Pink

Jeff Kravitz/FilmMagic

Pink was punk-rock chic while on the red carpet during the 44th Grammys.

23 of 27

Comeback Queen

Mariah Carey

Kevin Winter/Getty

Mariah Carey took the 2005 airwaves by storm with her album, The Emancipation of Mimi, which produced hits like "We Belong Together," "It's Like That," "Shake It Off," and more. So, when the 48th Annual Grammy Awards rolled around the next year, it was no surprise she walked away with three trophies.

24 of 27

The Cool Guys Club

Maroon 5

Carlo Allegri/Getty

Newly anointed superstars Maroon 5 kept their cool as they snagged the Best New Artist win in 2005.

25 of 27

Dangerously Iconic

Beyoncé

SGranitz/WireImage

In 2004, Beyoncé began her solo reign, snagging five of the six Grammys her debut album Dangerously in Love had been nominated for.

26 of 27

New Girl

Kelly Clarkson

Kevin Winter/Getty

Fresh off her American Idol win, Kelly Clarkson won the Best Pop Vocal Album and Best Female Pop Vocal Performance awards at the 2006 show for Breakaway.

27 of 27

Major First-Timer

Taylor Swift

Dan MacMedan/WireImage

Taylor Swift's Grammys debut was a huge success as the singer walked away with four awards — and became the youngest artist to win Best Country Album at the time — for Fearless.

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Source: “AOL Entertainment”