While I have the first Duets cd, for the most part, the whole "duet where someone isn't actually there" thing leaves me cold. I last listened to it a long, long time ago, and don't remember much from it in particular. I never got the second one.
There are a couple duets of that sort I like though; one is from Very Special Christmas 2. It's Cyndi Lauper horning in, no pun intended, on Frank's 1947 recording of "Santa Claus is Coming to Town." I love the original too, but I really like her voice and I think she adds a little something fun to it.
Another is actually from Duets; the theme from the movie "New York, New York," which is a classic, but still benefits from Tony Bennett's presence here. He sounds like he's having a ball, and who wouldn't be?
Speaking of Christmas duets, there's "We Wish You the Merriest," with Bing Crosby. I dislike Bing immensely, both as a human and a singer, and there are only two ways I can cope with him. If he's with the Andrews Sisters or Sinatra, he's diluted enough by more enjoyable performers that I can put up with him and not feel like punching him in the throat. This song is excellent, Frank is excellent, Bing ... is an extra voice. I can deal with that. This is pure midcentury Christmas, by the way; if you're looking for some Christmas music for your swingin' pad, download it.
He did two albums with Count Basie & his orchestra, and the second one, It Might as Well Be Swing," is highly recommended (in fact, I should be receiving my copy of it any day now) and having heard "I Wanna Be Around," I can see why. It starts out as a slow roll and blows into a big band finish, and makes a pretty sophisticated breakup song.
I don't know as much about the Brazilian musician Antonio Carlos Jobim as I probably should, but he was a contemporary, if not a counterpart of Sinatra's, and they did an album together, from which comes "Baubles, Bangles and Beads." I like bossa nova in general, and this song in particular, so this may be my next purchase.
And there is of course, his 1967 duet with his daughter, Nancy. "Somethin' Stupid," while admittedly a touch odd for a father/daughter song, is wistful and lovely, and their voices blend beautifully.
Frank Sinatra & Cyndi Lauper - Santa Claus is Coming to Town
Frank Sinatra & Tony Bennett - Theme from New York, New York
Frank Sinatra & Bing Crosby - We Wish You the Merriest
Frank Sinatra & Count Basie - I Wanna Be Around
Frank Sinatra & Antonio Carlos Jobim - Baubles, Bangles and Beads
Frank Sinatra & Nancy Sinatra - Somethin' Stupid