"Lenny" is a signature Stevie Ray Vaughan tune and reinstates the viability of the guitar instrumental in the 1980s and its infusion into modern blues and rock genres. A moody ballad from Vaughan classic 1983 debut album Texas Flood, the composition was named after his wife at the time, and presented the flamboyant Texas bluesman in a dramatically different setting.

"Lenny" is set in a slow floating tempo, contains a haunting chord-melody head, and is a simultaneous tribute to several of his influences: Jimi Hendrix, Curtis Mayfield and Wes Montgomery. The intro and head are clearly jazz-inflected. The use of Emaj13 and A6 in the main chord figure takes the normal I to IV change into more extended harmonic territory.