Just One of the Guys (1985)

Long before trans ideology became a trend for plenty of student bodies across the nation, cross-dressing was a sensation that existed mostly in comedies like Bringing Up Baby (1938), I Was a Male War Bride (1949), Some Like It Hot (1959), Victor Victoria (1982), Tootsie (1982), He’s My Girl (1987), Nobody’s Perfect (1990), Mrs. Doubtfire (1993), The Hot Chick (2002), and She’s the Man (2006). Of course, we’d be remiss not to include Just One of the Guys (1985) on this list. Lisa Gottlieb’s PG-13 flick features the jouncingly jugadocious Joyce Hyser as Terri Griffith, an aspiring high school journalist who goes undercover as a dude to prove a point (or two). Speaking of, sexy Sandy (Sherilyn Fenn) flaunts her cleavage via black lingerie! Meanwhile, Terri touts her curves in skimpy skivvies and a slinky bikini. Yet with the right clothes, haircut, voice and walk, Terri can appear to transform into a boy named Terry. Least ways, that’s what is perceived at school (aside from some close calls in the locker room and gym class). But trouble rears its twin torpedoes when Terry falls for her pal Rick (Clayton Rohner), a rare guy who is neither too macho nor too preppy. With the prom coming up, Terry feels a lot of pressure to come clean about her own personal Crying Game (1992). The climax arrives at the dance when the protagonist opens her tuxedo to reveal her bare breasts in front of everyone. It’s the greatest case of accessorizing since the cummerbund!