Road Trip Movies: Boys on the Side

NaNoWriMo is less than a month away, and this year I’m writing a friends to lovers road trip romance. In preparation, I am going to be watching all the road trip movies I can stand, and breaking them down per my favorite plotting structure: Joseph Campbell’s hero’s journey.

This week it’s the 1995 road trip tear-jerker, Boys on the Side.

Boys on the Side Movie Poster
Boys on the Side Movie Poster

From the Netflix synopsis:

“Looking to jump-start her career, lesbian night-club singer Jane (Whoopi Goldberg) answers an ad placed by a woman named Robin (Mary-Louise Parker), an AIDS sufferer who wants a companion to drive from the Big Apple to Los Angeles. En route, they pick up Jane’s friend Holly (Drew Barrymore), who’s pregnant and running from her abusive boyfriend. The trio gets as far as Arizona before Robin falls ill, and they must learn to rely on one another.”

Warning: Full spoilers ahead.

Ordinary World

Jane is singing in shitty bars in New York where the patrons laugh loudly through Jane’s rendition of Janis Joplin’s “Piece of My Heart.” Jane’s over it. She tells her guitarist she’s going to L.A.

Call to Adventure

Jane sees an ad in the paper: someone wants a driving companion from New York to the West Coast.

Refusal of the Call

Jane meets with Robin over coffee and decides she can’t drive cross country with a woman who listens to the Carpenters. (Hey, now!) The decision is made for Jane when her car gets towed. Robin is now her only way to get to L.A.

Meeting with the Mentor

No mentor. Jane and Robin bond for the first time, however, in a hotel room while watching The Way We Were. Robin confesses she longs for the romance in her life that she sees in the movies. Though Jane is a bit on the cynical side— she laughed during the “Your girl is lovely” sobfest scene—she tells Robin it could still happen for her.


Crossing the First Threshold

Jane makes a stop in Pittsburgh to visit an old friend, Holly. Holly is in the middle of a fight with her boyfriend over drug money. The boyfriend refuses to let Holly or Jane leave the apartment and gets violent. (I wish this scene had played better. A man knocking women around is serious stuff, but the scene doesn’t play serious. Maybe the director was going for darkly comical, but didn’t quite get there. The twisted humor in the classic Veronica Mars scene where Aaron Echolls beats the crap of out of his daughter’s lame-ass boyfriend it was not.)

Sweet little Carpenters-loving Robin pops in and attempts to negotiate with the druggie girlfriend-hitting dude until Holly hits him over the head with a bat and they tie him up and leave him. (He later frees himself from the bonds only to trip and give himself a fatal blow to the head.) The three women take the drug money and run, peeling off down the road to the tune of “Crossroads.”

Tests, Allies, Enemies

They find out that the worthless drug-dealing boyfriend died, making them fugitives. Holly reveals she is pregnant and is not entirely sure who the father is. There is a gabbing-in-the-car-on-the-road montage where Jane is doing most of the driving. Robin and Holly have a conversation in a diner while Jane sleeps in the car (probably because she’s tired from doing all that driving) and Holly reveals to Robin that Jane is gay and has a fatal flaw of falling for straight chicks.

Approach to the Innermost Cave (Approaching the Dark Moment)

Holly mentions to Jane that Robin looks sickly.

The Ordeal (Dark Moment)

Robin passes out in a bathroom in Arizona and is hospitalized. The nurse tells Jane that Robin has AIDS-induced pneumonia. Shit just got real. In one of many fantastic scenes between Whoopi Goldberg’s and Mary-Louise Parker’s characters, Robin breaks down, telling Jane she has nowhere to go.

The Reward

The trio set up house in Arizona. Jane falls into a community of musicians and free spirits, Robin has recovered and enjoys a flirtation with a cute bartender, and an increasingly pregnant Holly dates a besotted cop (Matthew McConaughey).

The Road Back (Return)

Jane and Robin’s friendship deepens. Jane expresses her love for Robin by finally acknowledging the awesomeness of the Carpenters and playing “Superstar” on her piano. Holly trusts her boyfriend too much and tells him about the mishap with the drug dealing ex in Pittsburgh. Jane tries to facilitate a romance between Robin and the bartender and reveals to him that Robin has AIDS. Robin is furious and cuts the man off before they can consummate. She and Jane have a huge fight and Jane moves out. Robin calls for her mother who gives her some speech about not keeping boys as side dishes that you stick a fork in when needed. (?!) Robin can’t bring herself to tell her mother that she has AIDS. Holly’s cop boyfriend turns her in and Holly gets arrested. Jane goes to Pittsburgh to help with Holly’s trial.

Video of the Carpenters performing “Superstar.” Yes.

The Resurrection (Climax)

Robin shows up in Pittsburgh to testify in Holly’s defense and reconciles with Jane, just in time to collapse into her final illness. In the hospital, Robin makes Jane promise to throw a big party after she dies. This is where the serious waterworks kick in. It’s one of Whoopi’s and Mary-Louise’s most awesome scenes together.

Return with the Elixir (Permanence of the Change)

Holly, the boy-loving flirt, has her baby and settles down with the cop. In a brilliant and touching bit (more blubbering on my part occurs) where a painfully thin, wheelchair-bound Robin begins singing “You Got It,” to Jane but Jane has to finish, Robin gives and receives love before she dies. Jane, significantly less sarcastic and defensive than she was in the beginning, continues on to L.A. by herself.

Clip of Jane singing “You Got It.” Warning: waterworks may ensue.

Additional comments

The premise of this movie is pretty fantastic. Whoopi is funny while seeming like she’s not even trying—several of her lines cracked me up—but then she turns around and breaks your heart. The soundtrack is the bomb. I knew so many of the songs and was just singing along. The central storyline is the strength of female friendship so major props for that alone.

Some of the other road trip movies I’m planning to watch and break down here are Take Me Home, Almost Famous, Little Miss Sunshine, Crossroads, and Thelma & Louise. Should be a fun trip!

What’s your favorite road trip movie?

5 thoughts on “Road Trip Movies: Boys on the Side

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