The first shows Tolkien in his study (at Merton, I assume).
The second shows an eight-story-high poster of Ian McKellan as Gandalf, hanging from the outside of a New Zealand post office.
The third, and most interesting of all, shows the storefront of London's infamous GANDALF'S GARDEN (described in the text as a "hippy cafe" and yoga center) -- I've heard about the magazine of the same name associated with this group, but hadn't known much about the associated store, which I'd vaguely assumed was a bookstore/head shop. Apparently no. Too bad the image is in black and white, since it's obviously a colourful spread.
And, as long as I'm commenting on the book's illos, I shd have mentioned the oddest one here:* what is, according to its caption, Rudolf Steiner's dust jacket design for Bulwer-Lytton's THE COMING RACE. I had no idea Steiner was an artist, as well as a world-class occultist. Given that Rudgley dates the drawing "c.1923", it must have been done at the v. end of Steiner's life. Interesting!
*and yes, that does include the photo of a nudist neopagan ceremony from the 'twenties. ick!