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Every Monkees Episode: “The Chaperone” (S1E9)

This past summer, we celebrated the 50th anniversary of the Monkees as a band by counting down our top 50 Monkees songs. Now, we’re celebrating The Monkees TV show by profiling each and every episode — exactly 50 years after it first premiered.

Tonight’s episode: “The Chaperone” (Season 1, Episode 9)

Air date: November 7, 1966

https://www.youtube.com/watch?v=v3ppv4eGsOo

“The Chaperone” is a pretty wild Monkees episode. Its humor and structure trades in some reliable tropes that the show used with aplomb during its two seasons. However, a lot is going on beneath the surface here that’s worth exploring.

The episode opens with the boys literally peeping through binoculars on Leslie Vanderberg (played by former Mouseketeer, Sherry Alberoni) a girl whom Davy is crushing on. This would be considered pretty creeper behavior in the modern day, but the Monkees get a pass here –because the Sixties!

When Davy approaches her to ask her out, he learns that her father is former General Vanderberg. He fought in World War II, and he’s super strict. Despite clever disguises as a magazine salesman or bomb shelter inspectors, the Monkees can’t seem to break into the fortress that is General Vanderberg’s house to continue to scam on his daughter.

What’s a lovelorn Monkee to do? Invite the Vanderbergs to a chaperoned party at the Monkees’ Pad, of course! The only problem is the meager chaperone candidates the Monkees wrangle are their unscrupulous landlord, Mr. Babbit, and their maid, Miss Weefers, who is… how do I put this lightly?… an alcoholic. Despite Davy’s best Henry Higgins-inspired efforts to make her a classier lady, Miss

Despite Davy’s best Henry Higgins-inspired efforts to make her a classier lady, Miss Weefers passes out in a drunken stupor right before the party. As it so often is in classic Monkees episodes, it’s up to Micky to save the day. He dresses up in some fab Bugs Bunny-style drag in order to masquerade as a chaperone named Mrs. Arcadian.

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Both General Vanderberg and Mr. Babbit vie for the affections of Mrs. Arcadian, who is secretly, of course, a crazy boy in a dress. I wonder how many young men at home had questioning feelings about seeing Micky Dolenz dressed in his get-up? He’s looking kind of sexy here, after all. To paraphrase the genius of Garth Algar, “Did you ever find Micky Dolenz attractive when he put on a dress and played a girl Monkee?” Party on, Micky, party on.

Although played for laughs in the traditional Looney Tunes-style, this plot is an early example of The Monkees dipping its adorable feet into drag and camp culture. One must remember that having a teen heartthrob cross-dressing for most of an episode of a nationally broadcast sitcom is quite a subversive act for 1966.

https://www.youtube.com/watch?v=pqUPLG4Jgo4

Also pretty wild is the lite psychedelic freakout of the party scene that happens as the episode continues. To the dulcet tones of the Carole King/Gerry Goffin-written “Take a Giant Step,” we’re treated to a cornucopia of weird party happenings, including cameos from Tarzan and Mr. Clean. If there can be one thing said about The Monkees as a show, its cultural references always come surprisingly from left field.

The core themes of the episode all come to a head (pun intended) at the end of this creative romp. As the kids are dancing and generally having a swell time, General Vanderberg discovers Mrs. Arcadian’s true identity and starts barking militaristic commands at them. The kids march in formation out of the party in a subtle, but effective, nod to the tumultuous political climate the Vietnam war had created just beyond the confines of the Monkees’ beach-house.

This leads to Leslie standing up to her dad and asking for some leniency when it comes to her dating life. Dear old General Dad is moved by his daughter and replies with a, “Well, why didn’t you say so? I’m not an unreasonable man,” in a coda that proves that maybe the gap between the generations wasn’t as big as either family member thought.

All in all, “The Chaperone” is a punchy little Monkees episode with some culturally relevant themes thrown into the mix. There’s not a lot of other TV shows of the era that would have allowed the gender fluidity that’s on display here. Even though drag is played for Some Like It Hot-style laughs (released just seven years earlier), there are other currents of gender and sexual identity flowing underneath the surface. Plus, the conflict between General Vanderberg and his swingin’ daughter is symbolic of the widening generation gap as the Sixties continued. Of course, beyond all this subtext, Micky’s looking totally cute in that dress, making “The Chaperone” a classic.

Louie Pearlman
Louie Pearlman is a comedic performer, songwriter, producer and pop culture writer living in NYC. He loves bubblegum music and punk in all its forms -- his favorite band is Talking Heads, but the Archies are a close second or third. You can check out his current projects at LouiePearlman.com, come see a show, and say “hi” after!