Tony Bennett (vocal)
The Essential Tony Bennett
There are so many things I can say about Tony Bennett. He truly is the one and only for me. He is compared to Frank Sinatra a lot and while justified (he even acknowledges and appreciates the comparison) I tend to enjoy Bennett's interpretation of the American Songbook more than Sinatra's. You can feel the heart and emotion in every note Tony sings.
Tony's most recent albums have revolved around themes (the blues, duets, etc.) more geared at gaining a mass appeal audience. That's fine but I think many would prefer to hear Tony in the more comfortable role of jazz singer and interpreter of great standards. With that said I would suggest two records that cover this perfectly, The Essential Tony Bennett and The Tony Bennett Bill Evans Album both on Columbia Records and Fantasy Records respectively.
The Essential covers everything up to the early 2000s and includes exactly the material you are looking for "I Left My Heart In San Francisco," "Rages To Riches," "The Best Is Yet To Come," and recent collaborations with K.D. Lang. Bennett Evans is a "core collection" type album, meaning you should definitely own it. Recorded at a time when Tony was very influenced by bebop, he went into a session with pianist Bill Evans and they came away with one the best vocal jazz albums of all time. If you really want to hear Tony in a different setting this is the album to listen to.
In recent years Tony Bennett's celebrity has overshadowed his musical contributions but there is no denying that he is a living legend and will be acknowledged as one of the best jazz singers of the last two centuries. A little raspy but consistently smooth, Tony Bennett continues be the embodiment of cool. Below are two cool clips featuring Tony with Bill Evans and a colloboration with Paul McCartney, K.D. Lang and Sting.