Chicago - The Band

Credit: Eli Watson
Credit: Eli Watson

I’m sure there are plenty of bands and musical acts that go through a radical transformation – but I would argue that Chicago has had the biggest change. Chicago has an album in the ’60s and also in ’08. If you randomly selected an album, you might like or hate what you get.

The Backstory of Chicago and Me

Chicago might have been a perfect band for my father. He was a rock and roll drummer in the ’60s and was your typical dad in the ’80s. His musical tastes and enjoyment of Chicago easily influenced my thoughts on the band.

Soft Rock Bill Hersey

As referenced in many articles, William (Bill) Hersey was a huge influence on my musical tastes. He often sat in his chair and listened to music – no outside distractions. He would just sit and rock. Sometimes he would be working on a TV or VCR (he was a television repairman and did side jobs at home). The smell of solder reminds me of soft rock.

VCR Repair - Bill Hersey - The Legend
William Hersey was a VCR Repairman and one damn good one. This relic is hard to find nowadays.

Although he had vinyl albums of all the classic rock groups, he had the CDs of many soft rock groups. I imagine he aged along with the bands. By the time I remember listening to these tunes from the other room, it was the mid-90s. He was in his forties. He had every Richard Marx album and I remember hearing plenty of Chicago.

It was no surprise when I started ranking songs, the Peter Cetera led songs were my favorites. They were very ’80s and that’s what I remember hearing. Granted, “Saturday in the Park” and “25 or 6 to 4” are amazing – but I love myself some soft rock.

Biology 102

There aren’t a tremendous of high school memories I have regarding the band Chicago – but one stands in my mind. I had Mr. Mutuska for sophomore Biology. I don’t remember much about that class, but for some reason we had computers. Maybe we did some research? More than likely, we goofed off on them.

This was 2000 and Napster was huge. Almost every computer had it installed. With Napster, came music. I was sitting next to one of my good friends, Shawn. I don’t know much about his musical tastes but he surely didn’t seem like a Chicago guy. My guess the song was already on the computer, but he started playing “You’re the Inspiration”. Being a ham, he started singing along and tried to get others in the class to join in. That power ballad will forever be linked to sophomore biology.

The Crash

One of the worst days of my life happened a few weeks earlier. Over the years, I developed an incredible music library. I had downloaded music since 1999 and many of those songs made their way onto data CDs. With the invent of external hard drives, I transferred my music to a 2-terabyte hard drive.

I threw away many of my old CDs. With iTunes and iPhones, I was never going to use them. I kept some of the sentimental albums, but most saw the garbage. Everything was on my hard drive. I would sync up my phone and grab my favorites and listen as I pleased. That hard drive had everything.

One day I tried to access a file I was working on. I was in the process of writing some short episodes for YouTube. My goal was to write 12 episodes and film. I would release like Netflix – all at once. I thought it was a unique way to see if people would binge watch on YouTube. The idea was original and I was up for trying something creative. For some reason, I couldn’t get the folder to my hard drive to open.

I switched outlets, power cords, computers, everything! The damn hard drive crashed.

My family photos were gone. All of my old graphics were gone. My music was gone.

Powerwashing with Chicago’s Greatest Hits

I turned to Pandora and streaming music. I wasn’t going to regain access to all of those songs. Illegal downloading was not something I would gamble with – I would either have to buy everything or stream. I decided on streaming.

Chicago Power Wash

One day I got sick of the commercials. Also, I wanted to listen to just one band. This was probably before Spotify became a thing. I decided that I wanted to hear Chicago. Not sure why, but I downloaded a greatest hits album. It was the only music on my phone.

That night, I had to powerwash behind the house. I decided to listen to some Chicago and power washed for a few hours. It was enjoyable. I could skip songs, repeat, and pause. I forgot that owning the music was better than streaming.

It was the start of me acquiring music again.

Chicago Now vs. Chicago Rank In 2007

I obviously had a hunch that I loved some Soft Rock in 2007. I wasn’t aware that there were such stark differences between the years, but I heard enough to know they had a rock side and a soft rock side. They put the exclamation point on my original top ten and pushed some major acts out of the way NOW.

Check out where they rank on my current list.

Chicago Metrics

By The Numbers



Chicago lands a great score – mostly because they hammered out those lovable soft rock hits in the mid-’80s. Double-digit five-star songs are nothing to sneeze. They put up a fight against some top acts – Pink Floyd and ELO, but some of their mediocre songs hurt the overall score.

A Deep Dive Into the Current Score

There are camps that like the early albums and there are people like me that love the Cetera soft rock albums. There is no doubt that there are classic and stinkers along the way. Chicago received some 1-star songs for just pure ‘noise’ tracks. They also put out a big-band-like record that was painful. Chicago 17, 18, and 19 – my jams.

Chicago Podcasts for Reference

The Chicago Band Podcasts

When Nerds Collide – After downloading tons of interviews from band members, I realized I just wanted to hear peoples opinions about the band. Typing in ‘Chicago’ in iTunes was a waste. All you found were podcasts about sports teams. Finally, I typed ‘Chicago Transit Authority’ and found a few podcasts related to the band. I landed on this podcast where two guys talk about the original album. They run out things to say about half-way through, but at least I found something besides a Danny Seraphine interview.

Welcome to Chicago – This was the podcast I was searching for. Full disclaimer: these guys aren’t the biggest Chicago fans, but for some reason, they decided to do an album by album podcast. I am down and I enjoy listening to the podcast and then listening to the album. They point out things I would have never noticed or cared about.

Chicago Videos for Reference

Chicago Netflix Documentary

VH1 Behind the Music – (YouTube) If you have seen one Behind the Music, you have seen them all. The teaser tells you the chilling story and then you watch the show to see what happens. It’s the same formula but works – if you only have 40-minutes.

Now More Than Ever: The History of Chicago – (Netflix) This documentary helped me get into the entire process of seeking out information about artists while listening to their albums. This film was entertaining and told a good story. You witness the band go from a rock band with horns to soft rock juggernauts.

The Terry Kath Experience – (Amazon Prime) This was a great looking and great look into the early days of the band. Terry Kath’s daughter sought out information about her dad (he died when she was two). This documentary focused on Terry, but you get plenty of Chicago.

The Battle of Chicago Albums

I don’t think I was surprised but I bet all of the classic rock guys are. If people actually reviewed this site, I might get tomatoes thrown at me. Yes, Chicago soft rock albums are the best. Sorry – not sorry.

Chicago 17360.00%
Chicago 19180.00%
Chicago 16120.00%
Chicago 18109.09%
Chicago VI90.00%
Chicago V80.00%
Chicago XI72.73%
Chicago XIV70.00%
Chicago 1360.00%
Chicago VII33.33%
Chicago X30.77%
Hot Streets30.00%
Chicago VIII30.00%
Twenty 125.00%
The Chicago Transit Authority16.67%
Chicago III8.70%
Chicago XXX8.33%
Chicago XXXII: Stone of Sisyphus9.09%
Night and Day: Big Band0.00%

The Greatest Hit from Chicago

It’s great when the hits come in with a perfect tournament number (2, 4, 8, 16, etc…). They landed 16 hits and we can use a standard tournament. I am sure we will see some old vs. new and see who comes out the victor.

This was honestly the toughest tournament so far. All of the songs were equal and it probably came down to daily preference.

Previous Greatest Hit and Tournament Outcome

“Saturday In The Park”

This came down to a tiebreaker and the reason “Saturday In The Park” won NOW is because it won in 2007. This was the only classic song that made it this far into the bracket. All of the others were Cetera ballads (granted, this was due to tournament placement). “Saturday In The Park” has the classic Chicago sound and just makes you feel good when you listen to it.


Chicago moved their way up the ranks and earned more love NOW than before. Their history was rather interesting and their progression from the ’70s rock to ’80s soft rock was a good one (for me). I have a new respect for the musicians (Terry Kath) and very curious to see what Cetera did in his solo career (I bet I am a fan). Chicago might be a guilty pleasure – but join the list (Journey, “Weird” Al, and Air Supply).


September 14, 2019

Some of Terry Kath’s early stuff might get an extra star, while some of the Cetera corny stuff might drop one. I guess it will depend on my mood when I hear the song again.