The Wonder Years Season 2 Episode 8 Review: Like a Boss
This piece was written during the 2023 WGA and SAG-AFTRA strikes. Without the labor of the writers and actors currently on strike, The Wonder Years being covered here wouldn’t exist.
The Wonder Years Season 2 Episode 8, “Like a Boss,” shines the spotlight on Lillian as she sets important boundaries at work, with a compelling performance from Saycon Sengbloh. Tim Young pens a serviceable script with solid direction from Michael Schultz. That said, it’s not the show’s strongest outing.
Perhaps it’s because there’s less of a focus on Dean. The last “Lillian in a professional setting” episode, Season 1 Episode 4, “The Workplace,” is one of the series’ best. As a character, Lillian is 100 percent capable of carrying an episode.
BILL: Nice try. Like I’m gonna let 13-year-olds play with a bunch of matches. Power saw’s in the shed.
While Dean should be a significant focus as the main character, anyone in the Williams family can drive the narrative forward. No, it’s the enhanced focus on Coach Cliff Long, a supporting character who usually fares better in an episodic B-plot storyline.

Allen Maldonado has terrific comedic timing and certainly delivers when the story calls for it. However, too much of a good thing can be a bad thing. Cliff, as a character, is most effective in small doses. In fact, he detracts from Lillian, whose arc is unarguably more essential.
Lillian’s story is an homage to the power of Black women and how they’re abused for emotional and mental labor. They’re the backbone of this country, who work tirelessly and thanklessly to keep things moving. Cliff takes advantage of Lillian’s friendship, while she fears setting boundaries because she doesn’t know how it’ll affect her position at work.
CLIFF: When you’re at your highest, is when the devil shows up.
“Like a Boss” presents a vital lesson for us all — the importance of establishing healthy boundaries — but it also illustrates how difficult it is for Black women (and people of color) to speak up without consequences or reprisals.

As for Dean’s plot, it doesn’t quite meet the bar. We don’t get enough time with Dean and Cory as they prepare for the soap box derby, so there’s no emotional payoff or resonance when the competition begins. Their soap box derby preparations could’ve been an entire episode.
Of course, writer Tim Young finds a way to connect the A and B plots using Cliff, which is a nice touch. Additionally, the outing delves into Lillian and Cliff’s relationship, and we don’t always get that kind of dynamic exploration.
LILLIAN: Cliff went up there and put on a show in front of God and everybody.
All in all, “Like a Boss” falls short, and while Saycon Sengbloh shines as usual, she deserves a stronger vehicle to showcase her talents. Perhaps more focus on why it’s challenging for women, especially Black women, to set boundaries, especially in the 1960s, would’ve driven the moral of this story home more successfully.

Stray Observations:
- I love that Bill let Dean and Cory play with a power saw but not matches. Ah, the ’60s.
- If there’s one thing you can count on, it’s the sympathy of your church … so long as they’re actually good people and not a-holes.
- I’d love to have Lillian as a boss. She gets stuff done.
- Knowing me, the minute I started that soap box derby race, my car would fall apart like I was in a cartoon.
- We’ve all had bosses like Lillian’s — someone who utilizes non-inflammatory language to ensure he’s not culpable. They’re the worst.
What did you think of this episode of The Wonder Years? Share your thoughts in the comments below!
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The Wonder Years airs Wednesdays at 9/8c on ABC, with next-day streaming on Hulu.
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