The majority of the lyrics for Uptown Special were written by Michael Chabon, the author of Wonder Boys and The Amazing Adventures of Kavalier & Clay. Ronson approached the novelist after turning up at a book signing in New York. "I wrote him a letter and he was just kind of instantly into it," he recalled to The Guardian.
Chabon fully immersed himself in the album's creation, working with Ronson and co-producer Jeff Bhasker (Kanye West, Drake, Alicia Keys). "He came down to the studio and it was like a Jeff Bhasker songwriting boot camp," Ronson recalled to The Observer. "You know, Jeff has all these amazing stringent policies on songs and what words sing good, and what you can't sing, how everything must adhere to the note, the chorus must start this interval higher than the verse, all these things. And Michael, obviously he has no problem in the words department, but he just seemed to love taking in all these songwriting boot camp ideas. He was incredibly patient."
The first set of lyrics that Chabon sent to Ronson were for this song. "As I started reading the words to the chorus ('Is this how you pictured it? Is this how you thought it would be?'), the melody began to form in my head at the very same time," Ronson recalled to The Guardian. "Melodies don't usually shoot into my head from nowhere like that, so it was like an amazing alley-oop pass to have these words."
Michael Chabon told NME about his lyric writing. "My understanding was Mark wanted me to create lyrics which had a point of view. Not lyrics from Mark's point of view, or my point of view - it was the point of view of characters - I thought he wanted songs with a narrative with a story."
"I wrote some lyrics and I sent it to Mark and Jeff Bhasker and I actually don't know what their first reaction was - it inspired Mark to sit down at the keyboard and try and put music to it, I don't think he'd had ever done that before. Those lyrics changed a lot over time. My first efforts were too hard to sing fundamentally. Those lyrics got edited, rewritten, cut down, two verses were cropped, they put a bridge in there. I had to work a lot on that. But that first song became 'Crack In The Pearl.'"
The closing track of Uptown Special is a second version of the song, "Crack in the Pearl, Pt. II
," featuring Stevie Wonder's harmonica.