The way I remember it, I am eight years old and playing Nintendo one Saturday morning when my father walks down the basement stairs to tell me about the play he and my mother saw the previous evening. He refers to the title as Say Yes, Pablo and notes that the play was supposed to be about Pablo Picasso but it was not really about anything, and in the place of normal dialogue there was a lot of chanting. He also said that 25 minutes into the show the first audience members exited out the back door, and the steady flow of unhappy patrons kept that back door open until the end.

Say Yes, Pablo holds a special meaing in our family. When we see a play that we really dislike, we say, “Well, at least it was better than Say Yes, Pablo.”

To set the record straight, the actual title of this 1987 Goodman production was She Always Said, Pablo, and the Chicago Tribune praised the play as “a striking achievement” while noting that there “is no ‘story’, as such.” In a twist of fate, my parents became acquaintances with Frank Galati, who conceived and directed She Always Said, Pablo although I doubt they ever initiated a conversation about that particular play.

Theater, like all entertainments, is a gamble. We pick a show based on criteria that appeal to us, and we usually know within 30 minutes where the show will fall on a wide spectrum ranging from “monumentally enlightening” to “exercise in mind-numbing endurance.”  Most of the shows I write about are on the plus side of this scale, but I also enjoy looking back at the many Say Yes, Pablo‘s in my past.  The ultimate hope in seeing a show is to gain a lasting memory, and each of these five shows (all of which had fans, I would imagine) has given me something to remember long after the curtain call.

[title of show] (Northlight) – 2011

I saw this show because… it had gotten positive word of mouth in New York

This musical had a reputation for being “The Little Show That Could.” It is a musical about making a musical.  Two songwriters and their two actress friends (in real life) decide to collaborate on an entry for the New York Musical Theater Festival, but the process of writing a show is more interesting to them than any of their other ideas (how torturous were their other ideas?). The most popular song states they would rather be “Nine people’s favorite thing / than 100 people’s ninth favorite thing.” The math does not add up because it is inconceivable that 109 people exist who would list this show in their top 10.

My lasting memory is… the uncomfortable feeling of spending 90 minutes trapped at a party with four close friends who keep laughing at their own inside jokes.

Jekyll and Hyde (National Tour) – 2013

I saw this show because… I liked the star, and I thought I liked musical

I had seen Constantine Maroulis in Rock of Ages three times, and he seemed like a good fit for the revival of this dark musical featuring some great songs. It turns out… whoever thought “This is the Moment” would be improved by a high-pitched rock arrangement was gravely mistaken. Yet, the greatest problems should be attributed to the production team, which created staging so dark and uncomfortable that the audience felt as though we were suffering through an un-ironic BDSM musical. (Don’t believe me? Watch this clip of “Bring on the Men.”) To add insult to injury, I had to choose between two pre-Broadway engagements that weekend. I chose Jekyll and Hyde, which closed on Broadway after 44 total performances. Kinky Boots, on the other hand, went on to play 2,541 total performances on Broadway.

My lasting memory is… bafflement as to why characters were always get tied up or strapped to things?

Days Like Today (Writer’s Theater) – 2014

I saw this show because… it got rave reviews from the Chicago press

If pressed to say which Chicago theater company most consistently produces exceptional work, my choice would be Writer’s Theater. Yet, the first production I saw at the company’s current venue was a rocky start. A woman in her early 20’s is left at the alter by her fiancé. She retreats to a vacation home, where her divorced parents show up with their respective new partners. The first act consists of an irritating rotation of Tessa singing songs about how she wants to be left alone and the four parents responding with songs about how she should tell them about her feelings. On top of that, she is clearly going to end up with the highly-educated pizza delivery guy, so forget about any suspense.

My lasting memory is… conviction that the early summer weather was more enticing than continuing to sit in the theater. (I went for a walk instead of watching the second act.)

Samsara (Victory Gardens) – 2015

I saw this show because… I usually enjoy plays and movies set in India

I have seen three of playwright Lauren Yee’s plays, and I found they all focused too much on off-beat pacing and not enough on characters. My least favorite of the three was Samsara. The subject matter is promising enough: an American couple chooses a surrogate mother from India to avoid the stricter regulations of the United States. But, it turns out, this is the kind of play where the unborn fetus (played by an adult) starts having arguments with his surrogate mother, a fantasy Frenchman keeps popping up for no reason, and the American couple is both racist and too stupid to use a video camera correctly.

My lasting memory is… unfounded hope that all of these strange ideas would meld into a meaningful ending.

Title and Deed (Lookingglass) – 2015

I saw this show because… Lookinglass’s record for producing outstanding visual theater

In hindsight, I should have had a better idea of what I was getting myself into before seeing Title and Deed.  The promotional blurb on Lookingglass’s website was one clue: “One man’s circuitous journey finds universal resonance in this compelling new travelogue… a whimsical and soul-searching meditation on life, language and our perennial search for home.” It is a 75-minute monologue by a character named Traveler, whose travels are at the metaphysical level. While musing about life and death, he stacks one observation on top of another. For example, our lives are insignificant moments sandwiched between “the human cannonball feeling at the beginning; the sickening thump at the end.”

My lasting memory is… resignation—whether the show was 10 minutes, 75 minutes, or four hours, I was not going to understand it.