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The Grammy Awards: A Philadelphia Timeline of Winners and Memorable Moments

From a rapper boycott to lots and lots and lots of Taylor Swift.


Philadelphia (and Philly-ish) Grammy Award winners DJ Jazzy Jeff and the Fresh Prince (aka Will Smith), Taylor Swift, and Jill Scott

Philadelphia (and Philly-ish) Grammy Award winners DJ Jazzy Jeff and the Fresh Prince (a.k.a. Will Smith), Taylor Swift, and Jill Scott / Photographs via Getty Images

With several Philly-ish artists—including Sabrina Carpenter, Taylor Swift, and Yannick Nézet-Séguin — up for Grammy Awards on February 2nd, we look back at some notable Philadelphia Grammy Award winners and Grammy moments from the past.

1962

The fourth installment of the Grammys saw the first major Philly wins: The Philadelphia Orchestra, and Chubby Checker, for “Let’s Twist Again.” Yes, we were just as obsessed with sequels then as we are now.

1965

The now-infamous Bill Cosby picked up the first of nine Grammys for his comedy album I Started Out as a Child.

1971

philadelphia grammy award winners

The supremely harmonious Delfonics hit it big in the R&B category with their enduring “Didn’t I (Blow Your Mind This Time).”

1973

North Philly’s Billy Paul had a thing going on at the Grammys with “Me and Mrs. Jones,” written by our own Gamble and Huff. Only Paul could make a song about infidelity sound so smooth and sweet and then get an award for it.

1983

Okay, Survivor was not from here. They were from Chicago. But this was the year that their “Eye of the Tiger,” from Rocky III, won, so we’re gonna claim it, as is our right.

1989

philadelphia grammy award winners

DJ Jazzy Jeff and the Fresh Prince, for “Parents Just Don’t Understand.” But the duo famously boycotted because the Grammys wouldn’t televise the rap segments. Booooo, Grammys!

1992

philadelphia grammy award winners

Finally, Patti LaBelle earned a Grammy — for her album Burnin’. Yeah, I have no memory of that either.

1995

Boyz II Men, for “I’ll Make Love to You.” They sang it at the ceremony, wearing pristine white suits, performing on a spinning stage, and getting the well-heeled crowd all hot and bothered.

2000

The Roots landed their first of three Grammys.

2002

philadelphia grammy award winners

Pride of Doylestown Pink scored her first Grammy — for “Lady Marmalade,” with Christina Aguilera, Lil’ Kim, and Mýa.

2005

Jill Scott, for her single “Cross My Mind.” Her first of three.

2010

These days, pride of Berks County Taylor Swift is a Grammy regular. Back in 2010, she was just winning her first. (Well, her first four.) And though she flies under the radar, Washington Square West classical composer Jennifer Higdon was honored with her first Grammy for a percussion concerto. She’s landed two more since.

2012

Taylor Swift, again. Jazz bassist Christian McBride got his first.

2018

The War On Drugs? Best Rock Album. Friends Central grad Benj Pasek? His Dear Evan Hansen Broadway score got him across the finish line. Meanwhile, local choir the Crossing saw its first of three awards.

2019

How is it that Jenkintown heartthrob Bradley Cooper has never received an Oscar but has found favor with the Grammys? This year, he won for “Shallow,” his A Star Is Born duet with Lady Gaga.

2022

R&B singer Jazmine Sullivan, for her Heaux Tales album. Yannick Nézet-Séguin (his first) and the Philadelphia Orchestra, for Best Orchestral Performance. And last but certainly not least, it’s Questlove! Everyone loved his excellent music documentary Summer of Soul.

2024

Getting tiresome, Taylor. Album of the Year. She’s up for it again this month.

Published as “The Grammys: A Philly Timeline” in the February 2025 issue of Philadelphia magazine.