Footage of Sinatra crooning on screen appeared as Keys sang and played the piano with a live orchestra at the event Sunday evening at Staples Center.
After performing with Ol' Blue Eyes, Keys then picked up the prize for Best Female R&B Performance for her song "No One."
Another highlight was the pairing of Beyonce and Tina Turner, who sang "Proud Mary" together.
Before the televised ceremonies began, West picked up three Grammys and Winehouse nabbed two.
Early in the telecast, Winehouse picked up Grammys for Best New Artist and Best Song for "Rehab," while West's "Graduation" was named Best Rap Album.
Foo Fighters' "Echoes, Silence, Patience and Grace" won the Best Rock Album Grammy, while Vince Gill's "These Days" was named Best Country Album.