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  • Harsher in Hindsight: Kevin Spacey as a sexual predator is pretty awkward these days in light of allegations against him. Though it does make Tess spraying him with a champagne bottle even more cathartic.
  • Magnificent Bitch: Katharine Parker is a Boston broker who transfers to New York and becomes the latest boss of chronic secretary Tess McGill. She assigns Tess with some menial tasks and at first expresses interest in Tess's idea for a merger between a business and a radio company, but then tells her it is not going to work while secretly planning to pass off the idea as her own. When Katharine catches wind of Tess having stolen the idea back, she exposes Tess's deception and nearly takes over her role in the planned merger as a result. Even when her boyfriend Jack Trainer falls for Tess and turns against her, Katharine keeps her cool and even maintains a graceful demeanor to avoid making a scene when about to ultimately lose her job.
  • Retroactive Recognition: Several actors who have since gone on to bigger and better things stand out in the cast list:
    • Alec Baldwin: 1988 was a big year for him. He entered the year with "Hey, It's That Guy" status, and then along came the John Hughes flick Shes Having A Baby, followed by Beetlejuice, Married to the Mob, and Working Girl. A little more than a year later he would break out into stardom as Jack Ryan in The Hunt for Red October.
    • David Duchovny: This was his first ever film credit. Look for him in the back of the closet in the upper left at Tess's surprise birthday party. See him again in the credits billed as one of four "Tess's Birthday Party Friends".
    • Oliver Platt: Tess's coworker Lutz from early in the movie, in only his 3rd ever movie credit.
    • Kevin Spacey: Coke-snorting Bob Speck from Arbitrage. Spacey was a last-minute replacement to play the role, being picked up in the limo with a copy of the script on the back seat for him to learn on the way to the shoot. He had a recurring role on the 1980s crime drama Wiseguy at the time, but mostly was doing bit parts in movies and one-off roles on other TV shows.
    • Joan Cusack as Tess's friend Cyn. Cusack was coming off the heels of her only season of Saturday Night Live (during a season that nearly got the show cancelled due to low ratings and bad reviews), as well as having a Starmaking Role in Broadcast News the previous year. She has worked steadily ever since in television and movies, including Toy Story, in which she provides the voice of Jessie the Cowgirl.
    • Nora Dunn as Ginny. This was the first movie Dunn ever appeared in. She was best known at the time for being a current regular on Saturday Night Live (and also being in the same cast as Joan Cusack, though, unlike Cusack, Dunn was popular and funny enough to stay on the show when it was being revamped for its 12th season). Dunn was on SNL from 1985-1990, where she was fired for refusing to appear in an episode hosted by misogynistic shock comedian Andrew "Dice" Clay. From then on, she's been in minor TV and film roles (for those who watch 1990s cartoons, you might know her as the voice of Histeria!'s meddlesome network censor, Lydia Karaoke).
    • Olympia Dukakis as the Personnel Director for Petty Marsh, who ends up placing Tess with Katharine Walker. Dukakis was most famous at the time for winning the Oscar for Best Supporting Actress playing Cher's mother in Moonstruck the previous year, and for being the cousin of 1988 Democratic Presidential Nominee Michael Dukakis. She went on to play roles in Steel Magnolias, the Look Who's Talking movies, and Mr. Holland's Opus.
    • A 19-year-old Ricki Lake as a bridesmaid at the Trask wedding. She's only on screen long enough to point out fellow bridesmaid "Bitsy" to Harrison Ford. Earlier in 1988 she played the lead role in John Waters' Hairspray, and went on to a long and steady career in television, including a eleven-year run as a talk show host.
  • Unintentional Period Piece: Katherine and Jack owning their own computers is used as a sign of how successful they are. Said computers are also naturally woefully outdated. And of course, the numerous shots of the Twin Towers, particularly in the opening and closing sequences.
  • Values Resonance: Katherine being a supposed feminist who wants to empower other women while having no issue exploiting for her own benefit and discarding them immediately after and still being part of a privileged upper class with money and connections is very relevant in the 2020's with increasing criticism of "girlboss" culture and it's effort to reframe as progressive how female CEO's who claim to be and even consider themselves feminists can be just as ruthless and callous as their male counterparts.

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