OK , I've given this some thought (!). I've gone for tracks that remind me of different phases of my life, which most guests do. In some cases I'm still torn between two choices.

1)Armstrong/Hines: Weather Bird. I got into jazz & blues when I first heard Armstrong on the radio when I was acout 9 or 10. Also got to get Earl in there somehow.
2)Jimmy Giuffre/Jim Hall: Train and the River. I first heard it at college in the possession of the guy who became my best man and still a good friend. I managed to source a secondhand copy myself later.
3)Roy Eldridge: I can't get started. From a JATP concert that I saw on tour in Birmingham. After I left college and got a job and bought a hi-fi this was the first record (2-LP set) I bought as I'd been to the concert and this was one of the highlights.
4)Salena Jones: Moment of Truth. When I was home from college and in the 2 separate years I worked in Birmingham I used to go to a jazz club called The Opposite Lock and they played this almost every night before the live bands started.
5)Chris Barber: Battersea Rain Dance OR Ken Colyer: One for my baby. To remind me of all those nights at the 100 Club in the 1970s. Colyer was the first artist I saw there in 1968 but Sheila bought me that Barber LP about the time we got engaged in 1970 so that wins out.
6)Alex Welsh Band: Blueberry Hill. We went to the 100 Club at least once a week when we lived in London and Alex was on about once a month. Much missed, great band.
7)Sinatra/Ellington: I Like the Sunrise. We were disapppointed when we saw Sinatra live- very perfunctory at the end of his career, Ellington never disappointed and great bands always inspired Sinatra to better things. An alternative would be any track by Ella with Oscar Peterson, two artists we never missed when they came to London.
8)SonnyBlack (Bill Boazman):Paris after Dark OR Lee Gibson: Misty. To remind me of the many happy hours I now have at Jagz club in Ascot, hard to choose between my current favourite blues and jazz artists.

There was a programme on BBC Radio called My Top 12 so I could add another four:
9)Humphrey Lyttelton: anything, probably one of the tracks with Elkie Brooks. We followed Humph a lot after Alex Welsh died, now he's gone.
10)Mississippi Fred: Baby Please Don't Go OR Sonny & Brownie: Long Way from Home. I've not managed to shoehorn enough blues into the list.
11)Basie: Splanky. That would wake me up & keep the beasties at bay.
12)Lonnie Donegan: Stranger Blues. One of his more authentic perfomances and would remind me of my teens.
Still no space for Animals: House of the Rising Sun to remins me of Greek holidays.
Book? I read so fast it would have to be a Complete Works of someone like Dickens. If a single volume then Grossmith's Diary of a Nobody always makes me laugh.
RtS
(Micca, can you get a solar powered Brennan (TM)? That would beat the I-Pod!)