Who Wore It Better? Risky Business Costume Edition

Business

The first Risky Business was one of the coolest movies to come out of the 1980s, but it was also full of great costumes that we’d love to see today. However, there’s just one problem — how can you be sure you’re really wearing it better than Tom Cruise? Let’s find out with this hilarious quiz on who wore the Risky Business costume better! A good sense of humor and a dislike of Tom Cruise are both required to take this quiz!

The movie

Perhaps no movie has a costume as iconic as Tom Cruise’s vest and tie ensemble from Risky Business. Who wore it better: Tom Cruise or Matthew McConaughey? Let’s find out! Some other famous risky business costumes include Ray Liotta’s silk robe from Goodfellas, Natalie Portman’s red dress in Closer, and that time George Clooney starred in an Oscar-winning movie called Up in The Air. All of these celebrities have proven that you can take a business risk with your attire, but does McConaughey match up to Cruise when it comes to wearing these risky outfits well?

The costumes

Long before their current publicity and internet meme status, Risky Business was a popular and widely regarded film. Starring Tom Cruise (aka: Super-wholesome-like) in his breakout role, his nerdy outcast character Joel Goodson puts on a costume and ends up having a ridiculously great night out with a prostitute played by Rebecca De Mornay (aka: pretty but harsh to look at). Rebecca De Mornay wore an unzipped shiny silver catsuit for her performance that was unlike anything seen before; her outfit is often cited as being ahead of its time. In many ways she redefined what sex appeal meant to women in film; previously it had been normal for female characters to be demure and reserved.

The cast

Kevin Spacey (1983) and Michael Fassbender (2013) both wore pretty similar costumes while filming Risky Business. Both men opted for a cream colored suit with shoulder pads. In addition, they both have nice heads of hair, but Mr. Fassbender’s is longer than Mr. Spacey’s – perhaps indicating that more time has passed since 1983 when Risky Business was released compared to 2013 when Michael Fassbender portrayed Frank T.J. Mackey in Frank. Let’s get into it… just who wears it better?

The main character – Joel Goodson (Tom Cruise)

Joel is about to graduate from high school and desperately wants to leave home. He wears his class ring on a chain around his neck as a constant reminder of everything he doesn’t want to be: Clerk. Lawyer. Dentist. Accountant. Maybe I could be a doctor, but how can you tell when everyone is lying on their back? This might sound like typical teenager stuff, but Joel has an added incentive: his father is an irredeemable jerk who constantly belittles him (and everyone else). So while Mr. Goodson wears black braces over perfectly good white shirts and goes off hunting every weekend with cronies, Joel sings along with Queen, raids Mr.

Miles Whitaker (Crispin Glover)

Costumes can make or break a character. They can alter your perspective, how you see yourself, and how others perceive you. Nowhere is that more evident than in Risky Business, where Tom Cruise’s initial character-defining moment is his decision to jump into his underwear and put on a pair of sunglasses while dancing with his friend. Even though he wouldn’t have won any costume contests otherwise (we are talking about a young Tom Cruise after all), it was enough to define him as that guy who danced around in his underwear in front of everyone when they should have been focused on driving home safely. We do not know what became of Crispin Glover or Miles Whitaker—they both disappeared immediately after their scene ended.

Lisa (Jennifer Grey)

In a neon green high-cut one-piece bathing suit and high heels, Grey’s portrayal of Frances Baby Houseman has you second guessing if it’s actually 1986 or 1986. We mean that in an extremely positive way. However, I feel like she could have taken her look even further with a matching neon colored blowout and some heavy eyeliner to complete her outfit…but that’s just me. Still, 9/10 points for effort because we absolutely love how she successfully channeled an ensemble right out of National Lampoon’s European Vacation.

Matty (Barry Miller)

If you like bad fashion, then Matty is your man. The lead character in 1985’s Risky Business wears tight white pants, an oversized blazer, and a turtleneck. The ensemble wouldn’t be considered daring by anyone except perhaps teenage girls—which makes it all-the-more unbelievable that his parents didn’t kill him on sight. You could pull off Matty’s look with a conservative suit jacket and sweater or button-down shirt under; think old newsman-style. Perhaps you could even add a pocket square if you want to keep things extra classic.

Zach/Loren Visser (Jerry Orbach)

Zack Morris from Saved by The Bell as Richard Gere in American Gigolo and Larry Daley from Night at The Museum as Roy O’Bannon in Coyote Ugly. While both Morris and Daley wear their costumes (Roy’s costume had him dressed as a real-life bartender, after all), neither of them do it quite like Gere. With his shirt unbuttoned down to his navel and, if memory serves me correctly, just a white tank top underneath (the same look he rocks in American Gigolo). And that is probably where I can draw most of my comparisons. See, Zack wears a black leather jacket over his light blue button-down dress shirt with tie combo.

Buddy (Jonathan Stark)

You know, I like your style. How about you come in here and we’ll see if we can take care of that [criminal] problem. Peter (Tom Cruise): And get paid for it? Buddy: Absolutely! What else is there in life, am I right? In other words, a riskier business is a business with more opportunity for profit – but one also comes with more potential for loss. And anyone who has seen Risky Business knows that it can be really risky to wear white after Labor Day… or to run an unlicensed escort service, for that matter!