Chicago’s career trajectory as a band is the equivalent of that guy you knew in college who was a bit of a hotshot and always there making his presence known at the biggest parties and campus demonstrations. When you catch up with him decades later you find he has moved to the most strait-laced town in your state, where he has ended up on the board of selectmen, voting down a new skateboard park or marijuana dispensary. Oh, how I kid the guys in Chicago. When this rock-group-with-horns busted out big-time from the Windy City, they were a septet known for their musical experimentation and leftie politics. But less than a decade later, on the cusp of the Reagan era, they were safe-as-milk mainstays of the Soft Rock category.

Yet the band’s keen pop sensibilities were already much in evidence on their dauntless debut, a double album released in April of 1969. Here, three Top 40 Billboard singles were in the mix along with the esoteric touches and long jams common to that period.

Chicago Transit Authority (which was then the band’s name until the actual CTA threatened legal action) opens with a lively mission statement called “Introduction” which is written and sung by guitarist Terry Kath. “Sit back and let us groove/And let us work on you, yeah,” cajoles the husky-voiced Kath and indeed the song’s arrangement follows what would become a tried-and-true formula they would develop with their producer James William Guercio. After a couple verses, the song takes off into an extended, multivariate instrumental section led off with by the horn section. This trio (Walter Parazaifer on sax, Lee Loughnane on trumpet and James Pankow on trombone) gave the group a jazzy cosmopolitan sheen that proved to have strong appeal. They yield to a solo by Kath, often the band’s ace-in-the hole, before coming back strong for a final verse where Terry notes on how they “turned around the mood/We hope it struck you different/And hope you feel moved.”

Well, something worked as the album’s next three songs were all hit singles and were all written and sung by keyboardist Robert Lamm.  The original side one is filled out by “Does Anybody Know What Time It Is?” and “Beginnings” both featuring strong melodies and vibrant playing. Listeners on the AM side may have been hearing these longish numbers in edited form as the piano prelude in the former song and the two-minute percussion outro in the latter were excised for the Casey Kasem crowd.

The hits keep on coming at the start of side two with “Questions 67 and 68,” with lead singing shared with bassist Peter Cetera. The song is also notable for the supple, momentum-driving drum fills of Danny Seraphine, who has never really gotten his full due as one of classic-rock’s great stickmen. From here on out, though, your results may vary. There is one more chart entry, a vigorous cover of the Spencer Davis Group’s “I’m a Man,” curiously released two years later as a double-sided single with “Questions 67 and 68.” Future adult-contemporary crooner Cetera helps out here with a muscular bass line and swapping out macho lead vocals with Lamm and Kath. But things also get pretty self-indulgent over the final two sides, starting with the seven-minute “Free Form Guitar.”

Terry Kath, who tragically died of an accidental gunshot to the head in 1978, was a major talent (and reputedly one of Jimi Hendrix’ favorite guitarists) but I’m not sure what justified this fingernails-on-blackboard exercise in musique concrete. But considering that Guercio devotes a whole paragraph to it in his immodest liner notes, I’m willing to shift the blame. It’s esp. confounding since “FFG” is bookended by two songs that showcase Kath’s torrid soloing within amenable blues-rock contexts: “Poem 58” and “South California Purples.”

After touching on the events of the previous year’s turbulent Democratic Convention in their hometown with “Someday” (with the inclusion of “The whole world is watching!” chant), the album ends with a brash free-form instrumental (credited to Pankow) called “Liberation” that clocks in at a healthy 15:41. While nowadays this jam may only appeal to Terry Kath completists and the odd speed freak, it does show a band willing to think big and take chances.

This spirit carried on to the next two albums (also double disc affairs) where adventurous compositions sat cheek by jowl with accessible rockin’ hits like “Make Me Smile” and “25 or 6 to 4.” Not content with three doubles, they upped the ante with the four-LP At Carnegie Hall, a lavishly-packaged and rather self-congratulatory box that only featured one new song. Their first single disc was 1972’s Chicago V (fans would become used to the Roman numerals and the band’s persistent curlicue logo) and what, for me, was an early red-flag on the song “Dialogue.” Although written by Robert Lamm, the song features a back-and-forth between a concerned college student (Kath) and a hedonistic friend (Peter Cetera, tellingly) that comes down on the side of complacency (“If you had my outlook, your feelings would be numb,” is Peter’s crowning comment). OK, maybe I’m reading too much into it, and Chicago did have a fistful of attractive hits on thru the mid-70s, like “Saturday in the Park” and “Feeling Stronger Every Day.”

But for many folks, especially rock geeks, the wheels came of the bus following the death of Terry Kath in early 1978. Although several original members remained, the band dabbled in disco but mostly became known for Peter Cetera’s treacly romantic numbers, which were indistinguishable from many other power ballads of the time from the likes of REO Speedwagon and Foreigner. Granted, this trend started before Kath’s passing (“If You Leave Me Now”) but steadily tracked downward with cliched love-song rhymes and sterile 80s production values featuring lots of electric piano. If you need examples, check out “Loser with a Broken Heart”, “Stay the Night” (don’t miss the absurd video!), and culminating in 1984’s mind-numbing “Hard Habit to Break” (from Chicago 17 if you’re keeping track). Cetera, probably miffed at having to share the profits at this point, left for a solo career shortly after.

Am I being too hard here? Chicago was not the only band from that era whose politics now seem like a fashion and whose target audience shifted from hard rock buffs to lovesick teenage girls and divorced single moms for whom songs like “Hard to Say I’m Sorry” was the purest poetry. You’re supposed to get more comfortable as you get older and for Chicago that meant hitting the summer-shed tour circuit with other mellowed-out acts like the Doobie Brothers, who started life as a de facto Hell’s Angels house band. So, to tweak the analogy I started with, Chicago Transit Authority is like that old hell-raising high-school buddy that you see again for the first time at your classes’ fortieth reunion. When you ask him what has been up to since then, he replies “nothing much.”

—Rick Ouellette