#Grammy

15 items

Video thumbnail — The Black Eyed Peas - Where Is The Love? (Official Music Video)
Celebrities 2003–2009 peak

Black Eyed Peas

An underground L.A. hip-hop crew added a singer named Fergie and became the sound coming out of every speaker in the 2000s. From "Where Is the Love?" to "I Gotta Feeling," the Black Eyed Peas owned graduation parties, sports arenas, and wedding dance floors for the better part of a decade.

Video thumbnail — Céline Dion - My Heart Will Go On (Official 25th Anniversary Alternate Music Video)
Celebrities 1990–2007 peak

Céline Dion

The Quebec girl who slept in a dresser drawer, won Eurovision, and ended the decade owning the biggest song in the world. Céline Dion's "My Heart Will Go On" topped the charts in more than 25 countries, Falling into You won Album of the Year, and then she went to Las Vegas and showed every pop star what a residency could be.

Video thumbnail — Train - Drops Of Jupiter (Tell Me) (Official 4K Video)
Music 2001

"Drops of Jupiter" by Train

She's back in the atmosphere with drops of Jupiter in her hair — the piano-and-strings ballad that soaked every radio format in 2001 and never really left. Pat Monahan wrote it after dreaming of his late mother, which is why a song about swimming through planets and fried chicken can still make people cry at a grocery store.

Video thumbnail — Fergie - Big Girls Don't Cry (Official Music Video)
Celebrities 2003–2009 peak

Fergie

Stacy Ann Ferguson went from Saturday-morning TV to the voice that powered the Black Eyed Peas' commercial earthquake, then walked straight into solo stardom in 2006. "London Bridge," "Glamorous," "Big Girls Don't Cry" — three Hot 100 chart-toppers off one album — sewed her into the fabric of 2000s pop.

Garth Brooks in a tuxedo at the 1991 Country Music Association Awards
Celebrities 1989–1998 peak

Garth Brooks

Garth Brooks made country music arena-sized. The wireless headset, the hit-after-hit albums, and "Friends in Low Places" became the sound of the '90s — country that didn't apologize for being enormous, and made it look like the point all along.

Video thumbnail — Alanis Morissette - Ironic (Official 4K Music Video)
Music 1995–1997

Alanis Morissette — Jagged Little Pill

Alanis Morissette's international debut detonated on alternative radio with "You Oughta Know" and never let up. At 21, she won the 1996 Grammy for Album of the Year, becoming the youngest recipient of that award at the time and selling over 33 million copies worldwide.

Video thumbnail — Lauryn Hill - Doo Wop (That Thing) (Official HD Video)
Music 1998–1999

Lauryn Hill — The Miseducation of Lauryn Hill

Lauryn Hill's solo debut album, a genre-blending masterpiece that merged hip-hop, neo-soul, and R&B into a landmark release. Released in August 1998, it featured the hit singles "Doo Wop (That Thing)" and "Ex-Factor," establishing Hill as a solo artist of remarkable range and depth.

Video thumbnail — OK Go - Here It Goes Again (Official Music Video)
Music 2006–2007

OK Go "Here It Goes Again" (the treadmill video)

Four guys, eight treadmills, one continuous take. OK Go's "Here It Goes Again" video cost about $4,000, was shot in Damian Kulash's sister's house in Orlando, and went up on YouTube on July 31, 2006, when the site was just starting to take off. It won a Grammy and showed the music business what a viral video could do.

Video thumbnail — The Wallflowers - One Headlight (Official Music Video)
Music 1996–1997

The Wallflowers — "One Headlight"

The melancholy glow of 1997 radio: Jakob Dylan—yes, that Dylan—singing about the death of ideas over the year's most inescapable groove. It topped every rock format at once, won two Grammys, and never even appeared on the Hot 100.

Video thumbnail — Outkast - Ms. Jackson (Official HD Video)
Celebrities 1994–2004 peak

OutKast

André 3000 and Big Boi met as teenagers at Lenox Square mall in Atlanta and launched one of hip-hop's most fearless acts. The South got something to say—literally—and hip-hop would never ignore it again.

Video thumbnail — Chamillionaire - Ridin' (Official Music Video) ft. Krayzie Bone
Music 2005–2006

Ridin'

A Houston rapper's song about profiling that climbed to No. 1, spent 31 weeks on the chart, and became the best-selling ringtone of 2006. "They see me rollin', they hatin'" echoed from every flip phone in America.

Video thumbnail — Sheryl Crow - All I Wanna Do
Celebrities 1994–2002 peak

Sheryl Crow

A former Missouri music teacher and Michael Jackson backup singer who broke through in 1994 with "All I Wanna Do," then followed it with "If It Makes You Happy," "Everyday Is a Winding Road" and "Soak Up the Sun." She won nine Grammys along the way.

Video thumbnail — Santana - Smooth (Official Video) ft. Rob Thomas
Music 1999–2000

Santana ft. Rob Thomas — "Smooth"

Man, it's a hot one. The Santana–Rob Thomas collaboration that refused to leave the radio, straddled the millennium at #1, and swept its Grammy categories. Decades later it's still the eternal-summer song the internet won't let die.

Video thumbnail — Shawn Colvin - Sunny Came Home
Music 1997–1998

Shawn Colvin — "Sunny Came Home"

Pretty, gentle, and secretly about a woman burning her house to the ground — Shawn Colvin's "Sunny Came Home" swept the 1998 Grammys, winning both Record of the Year and Song of the Year.

Video thumbnail — Toni Braxton - Un-Break My Heart (Official HD Video)
Celebrities 1993–2000 peak

Toni Braxton

The husky contralto behind "Another Sad Love Song," "Breathe Again" and "Un-Break My Heart," two eight-times-platinum albums in a row, and the ballad Billboard named, in 1998, the most successful solo song in Hot 100 history — one she didn't want to record.