Amy Winehouse on video: Five classic moments from her career

Though she only had two albums to her name at the time of her passing, singer Amy Winehouse made a deep impression on the pop culture universe thanks to the worldwide phenomenon that was her Grammy-sweeping 2006 album Back to Black.

For the better part of two years, Winehouse appeared on magazine covers, in concert, and all over television and radio promoting her album, which bridged the gap between old school soul, classic lounge attitude, and post-modern feminine toughness.

A series of self-destructive patterns followed her in the years hence, but Winehouse’s time at the top of the world still stands in these five great video moments.

1) Winehouse Wins Five Grammy Awards

Easily the high point in her career; Winehouse took home five statuettes at the 50th Annual Grammy Awards in February 2008 (Best Pop Vocal Album, Best Female Pop Vocal Performance, Best Song, Best Record and Best New Artist. She was inexplicably denied the Album of the Year prize by Herbie Hancock’s River: The Joni Letters, but her five victories put her in a tie for second place with Lauryn Hill, Beyoncé, Alison Krauss, Norah Jones and Alicia Keys for the most Grammy wins by a female solo artist in a single night).

Though she was performing via satellite from London—having run into visa issues prior to the show—she was by far the most popular artist in the room, and when Winehouse collaborator Tony Bennett announced Winehouse as the winner for Record of the Year, the singer was overcome with genuine shock and delivered a brief but poignant acceptance speech:

Her performances of “You Know I’m No Good” and “Rehab” are here:

2) Live At Lollapalooza 2007

In the heat of the Sunday afternoon sun in Chicago at 2007’s Lollapalooza in Chicago, Winehouse took the stage with her band and delivered a tour de force performance. Though she was never known as a consistent performer, she used her incredible pipes to great effect and owned the stage with her slinky, after-hours sexuality. Her performance of “You Know I’m No Good” is particularly memorable, as it begins with Winehouse singing almost to herself and slowly settling into the song as it goes on; you can actually watch her evolving in real time. (Her killer band helped, too.)

3) Live At Glastonbury 2007

While she was loved in the United States, Winehouse was positively adored in her home country, and her watershed performance at the 2007 Glastonbury Festival (the definitive European outdoor music festival) proved that she had her compatriots eating out of the palm of her hand. In front of a crowd of tens of thousands, she plowed through her already-large bevy of hits, including an especially sharp take on “Rehab.”

4) Cracking Jokes On Never Mind The Buzzcocks

In 2006, Winehouse was a guest on a long-running comedy show in England called Never Mind the Buzzcocks, which features musicians and comedians riffing on the current state of music. Winehouse more than holds her own in the format, casually dropping in gags about her own famous hair and Paris Hilton. She’s so easy-going and charming, you almost forget that she’s been through any kind of heartbreak at all.

5) Winehouse At 20

Right when her first album Frank was coming out, Winehouse appeared on a British talk show for a chat about jazz music and a performance of “I Heard Love Is Blind.” It’s a remarkable few minutes of television, and though she hadn’t yet developed the persona that would take Back to Black to incredible heights, you could tell that her charisma, her charm and her voice would serve her well.