Review: The Second City’s ‘Generation Gap…Or, How Many Millennials Does It Take to Teach a Baby Boomer to Text Generation X?’

The Second City’s Generation Gap is everything you’ve ever mocked your parents, grandparents, recent grad intern and tween niece for, but wittier and with better lighting.

Top Row L-R: Frank Caeti, Asia Martin, Maureen Boughey. Bottom Row L-R: Holly Walker, Evan Mills, Cody Dove. Photo by Teresa Castracane Photography.
The cast of The Second City’s Generation Gap. Top Row L-R: Frank Caeti, Asia Martin, Maureen Boughey. Bottom Row L-R: Holly Walker, Evan Mills, Cody Dove. Photo by Teresa Castracane Photography.

Generation Gap has you chuckling from the first reading of its perfectly descriptive alternate title: How Many Millennials Does It Take to Teach a Baby Boomer to Text Generation X? The comedy show by famed Chicago-based sketch comedy company The Second City is a collection of scripted sketches, improv bits, songs and quick scenes that in ways both hilarious and touching highlight the differences—and similarities—between generations.

Like Saturday Night Live, whose casts have included luminaries from The Second City (ex. Bill Murray, John Belushi, Amy Poehler, Tina Fey, etc.), Generation Gap pokes fun at aspects of our lives that could seem sad when looked at through a different lens. Meth addict at the aquarium? Or dad drinking scotch at a family lunch? Generation Gap’s take is hilarious.

The show works so well because of the smart, yet accessible script delivered by a talented six-person cast, whose ages are spread across generations. The “casts of the Second City” are given writing credits, with a special shout out to millennial Asia Martin, who is credited as a writer and the show’s creator. Martin plays the role of an empowered woman in several sketches, including responding to a creepy old man’s advances and facing off against the insecurities that arise from watching those three dots on iPhones that appear when another person is typing. She also briefly filled the role of Beyoncé during an improv bit at the performance I attended.

The Queen Bey is a popular subject throughout the show. During the clever “Mind the Generation Gap” game show sketch, a member of the audience born before 1970 had to complete Beyoncé lyrics, among other millennial challenges like sending a message completely in emojis. A 14-year-old boy was also a contestant, tasked with completing challenges like using a rotary phone.

The scripted cross-generational scenes are surprisingly touching, like the friendship between a grandmother and her openly gay grandson, who teaches her how to use Twitter. Another scene set in a nursing home with characters introduced in an earlier scene when they were much younger made me cry. Thank goodness it’s a comedy show, though, because just when I was about to lose it, I started laughing again.

Gen Xer Frank Caeti had me in stitches with his highly physical brand of comedy. He unabashedly exposes his muffin top and jumps around as a “feral boy” one minute, and the next, he’s getting just as many laughs with a deadpan delivery. Millennial Evan Mills also inspires LOL moments with physical humor—his ridiculous commitment to encompassing a character solely through the movements of his body in one scene at a Subaru dealership elicits one of the biggest laughs in the show.

Evan Mills and Holly Walker in The Second City's Generation Gap. Photo by Teresa Castracane Photography.
Evan Mills and Holly Walker in The Second City’s Generation Gap. Photo by Teresa Castracane Photography.

Millennial Maureen Boughey and Baby Boomers/Gen Xers Cody Dove and Holly Walker take on a lot of the “square” and older characters in the show, delivering nuanced performances that bring on smiles and giggles that start in the brain. Dove and Boughey are delightful as a couple that meets for the first time in a World War II-era bar. Walker, who was a performer and staff writer for Comedy Central’s The Nightly Show with Larry Wilmore, shines as a grandma and a creepy old man.

Director Anthony LeBlanc masterfully incorporates a variety of movement and uses the full span of the stage and simple, yet effective set of three doors surrounded by Windows 97-esque window panes (by Bob Knuth). Lighting design by Mary Keegan effectively creates different senses of place by lighting the windows with different colors—pastel tones to suggest a rococo 18th century France; an American flag in lights; or stars and fire for prehistoric times.

Generation Gap is the first of six original shows created as part of a partnership with The Kennedy Center. The goal is for the shows to tour beyond Washington D.C. and Chicago, which, based on the quality of Generation Gap, would be a gift for audiences outside of the DMV.

Running time: One hour and 30 minutes, with a 15-minute intermission.

Generation Gap, presented by The Second City in partnership with The Kennedy Center, plays through August 12, 2018, at The Kennedy Center, 2700 F St NW, Washington, DC. For tickets, purchase them online.

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Cassandra Miller
Cassandra Miller is a writer, editor, and publicist dedicated to amplifying the arts through her work as the president of CultuRally Communications and as a contributing writer to publications including DC Theater Arts, Baltimore magazine, Bmore Art and The Washington Post. After teaching English in Italy and the Czech Republic in her early 20s, she applied her journalism degree from Boston University to a position as a daily newspaper section editor and founder and editor-in-chief of an arts and entertainment alternative weekly in her native upstate New York before moving to Baltimore five years ago. She has more than 10 years experience working in the journalism and marketing/PR fields at organizations such as Baltimore Center Stage, the Greater Baltimore Committee, Visit Baltimore and The Washington Post. She has been in love with theater since she performed as both Maria and Mother Superior in a sixth-grade summer camp production of "The Sound of Music."


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