the soundtrack to the big lebowski is a good thing to have for segment 1.
The Big Lebowski (1998) - Soundtracks
i like using duke ellington tunes in this sort of context. you can't go wrong with flamingo, for example. herb jeffries adds an element of elegant cheese to any situation. plus the arrangement is great:
The Blanton-Webster Band by Duke Ellington - Rhapsody Music
and for part 2, while at work, i recommend my current (still) nominee for summer jam: