Apropos of nothing—not even some TikTok virality bullshit—Madonna has seen fit to reissue her 1985 single, “Gambler,” for all streaming platforms. Although Madonna has been rereleasing various remastered and remixed “goodies” lately (especially for Erotica’s thirtieth anniversary) in honor of going through her back catalogue with Warner Bros., “Gambler” is the most arbitrary pick to date. For it’s not as though the single has been reissued for the fortieth anniversary or some such. No, 2022 marks a rather unspecial thirty-seven years since the advent of Vision Quest and its soundtrack, for which Madonna offered up both “Gambler” and the more well-known “Crazy For You.” As for the former, Madonna, ever the ahead-of-her-time feminist, stated of the lyrical composition, “[It’s] really the girl’s point of view, because she’s, like, an unstoppable person… She doesn’t really need this guy.” Yes, it sounds exactly like herself she’s describing.
Except that, in Vision Quest’s case, it applies to the female lead, Carla (Linda Fiorentino), passing through Spokane, Washington on her way to San Francisco. She ends up boarding at high schooler Louden Swain’s (Matthew Modine) house after his father (Ronny Cox) rents a room to her. Despite coming across as the older, more mature woman (in real life, she’s a year younger than Modine), the attraction between her and Louden develops incrementally, all with the help of “Crazy For You” to soundtrack it. But the flipside to the vulnerability of such a ballad is “Gambler,” filled with the chutzpah and bravado that Madonna herself rose to fame on. Her own backstory, characterized by clawing her way to the top as a New York street rat, easily fits in with lyrics like, “Gambler/Yeah, I know all the words to say/‘Cause I’m a gambler/I only play the game to win, yeah” and “Don’t wanna say this but I think that I should/I’m better off forgotten if you think that I’ll be good/One day you see me, the next day I’m gone/Don’t fight me, baby, I don’t wanna hold on.”
Had Madonna been keeping a diary circa 1979-1982, these are lines that could surely have been ripped from its pages as she moved on from people like Dan Gilroy and Camille Barbone in her endless bid to break into the fame business. Indeed, “Gambler” couldn’t have been written with as much conviction as anyone except Madonna, complete with all her Leo arrogance as she goads, “You’re not happy with the way I act/You better turn around boy, don’t look back/You’re getting angry, you know I can see/You’re just jealous ’cause you can’t be me.” For a long time, of course, that was true, with every pop singer in the game yearning to have as much success and idol worship as Madonna. As time wore on, and she started to become viewed as more of a caricature of herself (particularly in her social media postings), jealousy has given way to something like “pity.” But of course, Madonna would never allow other people’s negative reactions to what she does stop her (hence, “you can’t stop me now”). Perhaps knowing more than ever that every behavior she engages in is a “gamble.” From rereleasing this little-appreciated single to rereleasing her Sex book in the climate of peak cancel culture.
No matter, for the theme song of Madonna’s life has been “Gambler.” With every move she’s made being one giant leap of faith starting from the moment she opted to drop out of college and move to NYC on a wing and a prayer. Thus, one can hear the genuineness of her earnest defiance as she makes the final declaration, “Yeah, I’m a gambler/That’s right, baby!” Although the single sounds better than ever, Madonna evaded giving the somewhat lackluster accompanying video an “HD” upgrade, leaving the look of it decidedly “lo-fi.” Which suits the aesthetics of the era perfectly as we see interspersed Vision Quest scenes attached to Madonna’s nightclub performance in the movie. Indeed, she’s billed as “Singer at Club” in the credits, yet another nod to the grind of her early days spent performing in dives throughout the Eastern Seaboard. A grueling slog she was eager to transform into a national tour once she hit the bona fide big-time with her second album, Like A Virgin.
So it was that “Gambler” managed to make the cut for the setlist of 1985’s The Virgin Tour. Yet, although the tour kicked off on April 10 in Seattle, “Gambler” wouldn’t get an official release as the second single from the Vision Quest Soundtrack until September of ’85. So clearly, Madonna believed in it enough to do some ample pre-promoting throughout the tour, wherein she appears for the only live rendition of the song dressed in simple skin-tight black leggings, a black crop top with a cross cutout at the chest and arm-length black fringe gloves. Relying solely on her raw stripper energy, Madonna dances about in the manner she became known for in early videos like “Everybody” and “Lucky Star” as she asks, “You understand what I’m talkin’ about, Detroit?” (with the sole official recording of the show having taken place in her hometown).
Not only did she make Detroit understand all about the undiluted ambition emanating off her in “Gambler,” but the entire rest of the world. Produced by then-boyfriend John “Jellybean” Benitez (who Madonna would throw over in 1985 for Sean Penn), this single ultimately needs no “reason” to be rereleased. For it not only distills, but cuts to the core of Madonna’s entire identity—the very one that has landed her where she is today.
