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Monk’s first record for Columbia could be accused of being a safe bet since it features a selection of classic Monk tunes instead of new material. However, don’t dismiss it too quickly. On the original recordings of these songs, the pianist played as if he was chiseling the tunes out of marble, and part of the fun was listening to what seemed very much like composition in progress. These recordings, on the other hand, sound more like finished sculptures or polished works of art.
Perhaps Monk sensed that this would be the last time he would record these tunes in the studio, or maybe Macero gave him more takes to hone a flawless performance. Nevertheless, Criss Cross was (and is) a great way for listeners unfamiliar with Monk to experience him for the first time in slightly low-key performances of classic Monk tunes. None of the songs exceeds four minutes and offer an excellent cross section of Monk’s artistry, from the lively “Hackensack” to the artfully constructed “Criss Cross” with a couple of standards thrown in, of course. “Crepuscle With Nellie” is arguably the best rendition of the tune, with Charlie Rouse displaying an empathy and understanding that not even Sonny Rollins could find. Monk may have had more interesting sidemen in his past, but Rouse gave the group a reliability it previously never had. However, “Pannonica” (not on the original LP release but added as a bonus track to the previous CD reissue) meanders too long and “Coming on the Hudson” (a brand new bonus track for this release) is a complicated tune on which not even Rouse can find footing. At any rate, an excellent fresh start.
I love jazz because anything is possible; it has few rules and the best jazz breaks those ones. I prefer free improv because it doesn't really have any rules at all.
I was first exposed to jazz in my teens (in the late sixties).
The first jazz record I bought was Filles de Kilimanjaro by Miles Davis, shortly followed by Extrapolation by John McLaughlin.
My advice to new listeners is to listen as widely as possible and not to make snap judgments--stick with it.