Hello, and thanks for the question.
Although in informal, conversational grammar one will often hear the preposition "of" used to link an adjective with a noun, this construction is usually technically incorrect. The preposition "of" should only be used with a quantitative modifier of a noun—for example, "How much of the movie did you watch?" So, "How detailed a song list did you provide to the DJ?" would be the best choice of the two. Alternately, the question could be phrased as, "How detailed was the song list that you gave to the DJ?"
Hope this helps!