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"Plaid" from Stone of Sisyphus: For years this track was only available to the bootleg-buying public, as it was recorded for Chicago's up-until-recently shelved 1994 recording, Stone of Sisyphus. The entire Stone of Sisyphus project was something of a revolt against the power ballads and made-to-order Diane Warren hits that had comprised the band's greatest successes during the late 80s after Peter Cetera's departure. Moody, atmospheric and infused with Champlin's blue-eyed soul, this song could have signaled a bolder artistic direction for Chicago. Smoldering with the frustration of playing the same greatest hits on the Oldies circuit, it provided a rudimentary blueprint of breaking out of that vicious cycle. Sadly, Stone of Sisyphus was rejected by their record company, and the band turned to a big band cover album and a series of "Greatest Hits + 2 New Songs" for the rest of the 1990s. Already frustrated with the band's stagnant concert performances, Champlin would stick it out for another 15 years before finally calling it quits in 2009 and rededicating himself to his solo career.
"A Hit By Varese" from Chicago V: The Chicago V album was a massive success, topping the charts for nine weeks, and finding the band in a moment of transition between it's more ambitious origins and its string of Top 40 radio dominance that would continue throughout the Nixon-Ford years. The song complains about the straitjacket qualities of writing a hit single, and the song itself thwarts those very conventions. Borrowing traits from the song's namesake, avant-garde composer Edgar Varese, all three horn guys are given atonal solos to mix up the piece, which is written in what appears to be 12/8 time. This is a bold-as-brass way to start the record whose big hit was "Saturday in the Park"! Like "Plaid" the irony of Chicago publicly chafing against record industry convention would become more evident in the following years. One of the great shocks of my life was when the band dusted this one off during a 2001 concert performance. "Hold On" from Chicago XIV: Before he became known primarily as a balladeer, Peter Cetera insisted that he was a rock and roller, who was rarely given a chance to perform such material with Chicago. This song suggests that he might well have been correct and this song merges Cetera's rock aspirations with his melodic instincts. Even in lesser efforts, Cetera was capable of generating at least two or three distinct hooks to make a given song memorable. "Hold On" does this, and it does this without relying on Chicago's horn sections for anything more than occasional window-dressing. Unfortunately, very few ever heard this song. As Jimmy Pankow once joked, Chicago XIV went aluminum; maybe plywood. For a song in a similar, but less forceful vein, consult "Gone Long Gone" from the otherwise ill-fated Hot Streets album. Cetera's upbeat song here is like a cross between the harmonies of America and the lead guitar of George Harrison.
"Oh, Thank You Great Spirit" from Chicago VIII: On this striking track, Terry Kath channels his inner Hendrix to create a foggy, ethereal song that follows a man's realization that he has died. The song just goes off the deep end in the last two minutesis this symbolic of the void of death? the journey to the next life? Only Kath knows the answer, and he ain't tellin.'
"Ballet for a Girl in Buchanan" from Chicago II. This is a lengthy suite written by trombonist James Pankow and monopolizes the second side of the band's sophomore release. You have probably already heard two of the composite pieces of this effort, the hit singles "Make Me Smile" and "Colour My World." These two songs lose much of their flavor and context, however, if listened to independent of the entire Ballet. Pankow switches styles with abandon, putting baroque sections in the "West Virginia Fantasies" movement, while emulating Copland in the section titled "Anxiety's Moment." A more stylistically diverse effort in the same vein of the Abbey Road medley, Pankow gambles and it pays off.
Other considerations: "Poem 58," "Now That You've Gone," "The Pull," "Lovin' Chains," and "In The Country."
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.