Two records that show why Wes Montgomery's guitar sound was simply unmatched in jazz.
Pretty Blue is a two-fer compilation that gathers some of Wes Montgomery's finest small group work, and it's a straightforward way to hear what made his guitar playing so immediately recognizable and utterly compelling. His approach was distinctive in the most practical sense—those octaves, that warmth, the way he could make an electric guitar sound like it was conversing with you rather than showing off. There's no filtering or pretense here; this is Wes doing what he did best in intimate settings where every note counts.
What strikes you listening through these sessions is the consistency of his phrasing and touch. Whether he's playing a ballad or something uptempo, there's a singing quality to his lines that feels closer to vocalists than to most guitarists. The rhythm section locks in around him with purpose, and Wes never overplays—he seems content to let space breathe in a solo, which was becoming rarer in jazz at the time. You hear him thinking through each phrase rather than running changes, and that restraint is exactly what makes him so easy to listen to across multiple plays.
This isn't his most celebrated period, and it's not the place to start if you're new to Wes—try The Incredible Jazz Guitar of Wes Montgomery (1960) first for a fuller picture of his artistry. But Pretty Blue is the kind of record that justifies why musicians and serious listeners have always held him in such high regard. It's straightforward, unpretentious jazz that simply swings, and that's more than enough.