Wearing a sly smile as she performed for a small cabaret audience, Winehouse gave a sultry, soulful rendition of the hit that has defined her recent fall from grace. She looked just as coy as she sang the song "You Know I'm No Good" - almost reveling in the irony of her words.
But she seemed dumbfounded when she was announced as the record of the year winner. She was immediately enveloped by her band, then her mother and father, who have publicly worried whether Winehouse who recently entered a drug rehabilitation center after months of erratic behavior and canceled performances - would survive her demons.
"I'd like to thank the Academy for courageously breaking the mold this time. In doing so, honoring the giants upon whose shoulders I stand, some of whom like Miles Davis, John Coltrane ... unquestionably, deserved the award in the past. But this is a new day, that proves that the impossible can be made possible."
"Last night I saw you in my dreams, and now I can't wait to go to sleep," sang West, dressed in all black and with MAMA etched into his haircut, as he launched into "Hey Mama," a celebratory tune from his second album that has now turned into a somber ode.
2He won awards for best rap album for "Graduation," best solo performance for "Stronger," best rap song for "Good Life" and best rap performance by a duo or group for his collaboration with Common on "Southside."
When West accepted the best rap album trophy, the orchestra was trying to play him off the stage when he began speaking about his mother.
"It would be in good taste to stop the music," West said - and the music stopped.
"I know you're really proud of me right now and I know you want me to be the No. 1 artist in the world and Mama," West continued, "all I'm going to do is keep making you proud. We run this."
The Grammys, celebrating its 50th year, emphasized its history from the first performance. Alicia Keys, glammed-up with a '50s style, sat at the piano and sang "Learnin' the Blues" along with a black-and-white video performance from the late Frank Sinatra.
"Frank Sinatra looked good for 150, didn't he," Prince joked moments later before introducing Keys as the best female R&B vocal winner for her smash "No One."
Later, the casts from Cirque Du Soleil's "Love" Beatles' show and the Beatles-inspired movie "Across the Universe" paid tribute to the Fab Four as Ringo Starr, Yoko Ono and George Harrison's widow Olivia Harrison watched from the audience.
It was a hot-legs competition when Tina Turner teamed up with Beyonce on "Proud Mary." The senior citizen kept up with her younger counterpart, showcasing her famous dance moves while wearing a tight-fitting silver bustier and pantsuit.
Carrie Underwood earned two Grammys, including for best female country vocal performance. Bruce Springsteen took three awards, including best rock song for "Radio Nowhere." Other winners included the White Stripes, Justin Timberlake and Mary J. Blige with two each, the Foo Fighters, Herbie Hancock and even Democratic presidential candidate Barack Obama for best spoken-word album.
In any other year, West would have been the main storyline thanks to his history of awards-show tirades, his huge album "Graduation" and the shocking death of his mother. But the absent Winehouse, up for six trophies, upstaged West and everyone else.
The 24-year-old singer-songwriter's personal life has fallen apart over the past year as her career blossomed. As the ceremony approached, suspense built over whether she would appear. She was rejected Thursday for a U.S. work visa, and Grammy producers arranged for her to perform via telecast. On Friday, the U.S. government reversed itself and approved Winehouse, but it was too late for her to make the cross-continental trek.
By Nekesa Mumbi Moody