In this episode of The Shermer High Alumni Association, we’re pouring ourselves into the neon-soaked, flair-bartending mess that is Cocktail (1988). From Tom Cruise’s Bryan Flanagan chasing big dreams in New York, to Bryan Brown as the charmingly cynical mentor, to Elisabeth Shue as the grounded love interest, this movie delivers high drama, questionable career choices, and enough Blue Hawaiians to make your liver nervous.

We talk about its rollercoaster of ambition, romance, and beach bar antics, the infamous bar-top poetry scenes, and whether this glossy 80s cocktail still goes down smooth. Where will it score on the Cringe Meter?

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The journey continues as Pee-Wee’s wild cross-country search for his beloved bike reaches peak campiness. We break down the Alamo tour (spoiler: no basement), the biker gang showdown, and the gloriously meta movie-within-a-movie ending. Along the way, we celebrate Paul Reubens’ comedic genius, explore the film’s lasting cult appeal, and revel in the strange, wonderful world Tim Burton built. Whether you first saw it on VHS or just discovered it, this is one road trip worth rewinding.

Grab your bowtie and hop on your bike: this week, we dive into Tim Burton’s delightfully bizarre 1985 classic, Pee-Wee’s Big Adventure. From Pee-Wee’s legendary breakfast contraption to his epic quest for a stolen bike, we revisit the film’s offbeat humor, surreal set pieces, and the iconic characters that made it unforgettable. We’ll gush over Paul Reubens’ pure commitment to the role, Dottie’s loyal charm, and of course, Large Marge’s nightmare fuel. It’s absurd, it’s brilliant, and yes, we are still obsessed with it.

We locked ourselves in the attic to rewatch the 1987 adaptation of Flowers in the Attic, and honestly? We’re still recovering.

This week, we take on V.C. Andrews’ gothic cult classic, where a grieving mother hides her children in a mansion attic, a villainous grandmother weaponizes religion, and a bridal veil becomes a murder weapon. From powdered donuts to plot holes, we’re unpacking all the trauma, tropes, and twisted family dynamics this '80s movie has to offer.

Spoiler: this one gets dark. But don't worry, we're bringing our usual sarcasm, side-eye, and Gen X survival humor with us.

Content Warning: This episode discusses themes of child abuse, trauma, incest, and death.

What do you get when you mix Greek mythology, a disco roller rink, Gene Kelly, and Olivia Newton-John glowing like a cosmic fairy? Well, apparently... Xanadu.

This week, we try to make sense of the gloriously chaotic cult classic that sparkles, spins, and confuses in equal measure. With a plot that feels like it was sketched out on a coke mirror and music that somehow still slaps, Xanadu might be the most “so bad it’s great” movie we've rewatched yet.

Roll with us. It’s weird, it’s glittery, it’s Xanadu.

In 1982, Tootsie earned 10 Oscar nominations, making Dustin Hoffman a household name (again).

This week, we rewind to the chaotic charm of Tootsie—a film where one man’s desperation turns into daytime TV stardom, unintentional social commentary, and a baby named Amy.

We break down:

• Hoffman's method acting… as a woman

• And whether Tootsie is still progressive, problematic, or just plain entertaining

It’s time.... to talk wigs, male egos, and soap operas.

A flat tire, a Playboy magazine, a stolen car, and an impromptu blues performance—just another normal night of babysitting in 1987… right?

This week, we’re revisiting Adventures in Babysitting, the chaotic cult favorite that gave us Elisabeth Shue, Thor worship, and a truly absurd tour of late-80s Chicago. But between the nostalgia and the neon, this movie also serves up some major cringe—especially in the racial stereotyping department.

We talk:

• Babysitting as a high school senior

• Each character's questionable decision-making

• The moments that still made us laugh

• And the ones that aged like a forgotten hot dog under the car seat

Five teens walk into detention... and somehow walk out with emotional trauma, a makeover scene we’re still annoyed about, and one of the most quoted movies of all time.

This week, we’re revisiting The Breakfast Club—John Hughes' iconic coming-of-age film that shaped a generation and launched a thousand think pieces. But how well does it really hold up?

We break down:

• Whether Bender is charming, damaged… or just a walking red flag

• That infamous lipstick trick (WHY)

• The moments that still hit—and the ones that aged like spoiled milk

• And why Ally Sheedy deserved better

It’s raw, it’s real, it’s full of Gen X angst—and we have thoughts.

Some movies age like fine wine.
And some age like a humanoid duck with a questionable libido.

In this episode, we dive headfirst into Howard the Duck (1986)—a high-budget, high-concept, low-explanation film that somehow features space travel, duck boobs, demon possession, and Lea Thompson in full 80s rockstar mode.

We break down:

• The truly bizarre plot that nobody signed up for

• The animatronic phenomenon that was Howard

• Why Lea Thompson remains an absolute queen despite everything

• And the parts that made us laugh, cringe, and stare at the screen in open-mouthed confusion

Yes, it’s messy. Yes, we have notes. But we still kinda love it.

Because if we survived this movie as kids… we can survive anything.

The questionable choices continue as we return to Rydell High for Part 2 of our Grease 2 rewatch—and trust us, things go completely off the rails (and we’re so here for it).

This episode picks up right before the deeply confusing, mildly horrifying “Do It for Our Country” number. From there, we dig into the second half of the movie: more musical chaos, a motorcycle makeover that defies physics, and a pep rally that somehow turns into a over the top romantic reckoning.