This Underrated Comedy Saw Robert Downey Jr. Meet His Match in Molly Ringwald

Although the term “Brat Pack” wasn’t officially coined until a New York story ran in the summer of 1985, many of the unofficial “members” of the troupe had appeared together in several films throughout the decades. Young stars like Emilio Estevez, Jon Cryer, Andrew McCarthy, Judd Nelson, Demi Moore, and Ally Sheedy, among others, became quite popular through a series of films that touched on their experiences growing up and maturing. While many films like Pretty in Pink and The Breakfast Club were met with critical acclaim, backlash against the “Brat Pack” began to emerge in the aftermath of the failure of St. Elmo’s Fire. Brat Pack films made in the aftermath were not generally met with as warm responses, but Robert Downey Jr. joined Molly Ringwald for an underrated Brat Pack comedy, The Pick-up Artist.

Brat Pack films had initially been largely set in high school, as films like Sixteen Candles and The Outsiders spoke to the adolescent experience in a way that appealed to younger viewers. However, the Brat Pack stars began to grow up, and many of their subsequent efforts to take on more “serious” projects about young adulthood lacked the comedic charm that had made their earlier projects so successful as coming-of-age movies. However, The Pick-up Artist was a refreshingly mature Brat Pack film that retained the group’s more compelling origins. It’s ultimately a film about the uncomfortable transition between childhood and adulthood, and how the process of maturation is by no means an overnight one.

The Pick-up Artist

A womanizer meets his match when he falls for a woman in debt to the mafia.

Actors

Molly Ringwald, Robert Downey, Dennis Hopper, Harvey Keitel, Danny Aiello

Release Date

September 18, 1987

Run Time

81 minutes

Director

James Toback

Studio

20th Century Fox

What Is ‘The Pick-up Artist’ About?

Downey Jr. stars as the 21-year-old womanizer Jack Jericho, who works part-time at a university where he will often charm his students. Jack seems to pride himself on the ability to “pick up” young women, but never get in a serious relationship. He’s terrified of any deep commitment that could in any way put his carefree lifestyle to an end. However, Jack begins to slip up when he shares a brief encounter with the museum tour guide Randy Jensen (Ringwald), who he instantly falls head over heels for. When Randy rebuffs his initial advances, Jack is forced to determine how good he actually is, and whether “giving up” his womanizing lifestyle is worth it for a girl he really has feelings for.

Although he showed early signs of the signature charisma that would define his work as Tony Stark in the Marvel Cinematic Universe, Downey Jr. succeeds in giving a more sensitive performance in The Pick-up Artist. Jack is forced to cope with the cold reality that he can’t simply coast on his personability for the rest of his life, as one day he will have to start taking things seriously. His dynamic with Ringwald is quite interesting, because she is the first character who isn’t willing to put up with his nonsense and sexism. Jack is forced to work hard on himself to drop his toxic traits; this makes the film more unorthodox as a romantic comedy.

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The Pick-up Artist indicated that Ringwald had matured as an actress since her breakout roles in Sixteen Candles and The Breakfast Club. While those films cast her as shy, naive high school student learning to take confidence in herself, Ringwald does a great job at showing how Randy has pride in her profession and life decisions. The film needed a female lead who could match the kinetic energy that Downey Jr. was bringing, and Ringwald succeeded in one of her better performances.

‘The Pick-up Artist’ Was a More Mature Brat Pack Film

The banter between Downey Jr. and Ringwald is uniformly excellent, but The Pick-up Artist takes a mature look at growing up. Both Jack and Randy have graduated from high school, but haven’t quite learned how to adjust to being entirely independent. Jack doesn’t have a parental figure who can reign in his erratic behavior, and Randy is not interested in asking for help, even when she really needs it. The connection they form isn’t just a romantic one, but a recognition that, as young people, they still don’t know entirely what they are doing. It’s impressive that a film with this much crude sexual humor is able to end at such a charming, borderline saccharine moment.

The Pick-up Artist also features a mature subplot featuring Randy’s father, who is played in a scene-stealing performance by Dennis Hopper. A serial gambler and raging alcoholic, Randy’s father, Flash, ends up getting Jack in trouble with the mob. Although the serious turn could’ve derailed what is generally a fairly light-hearted romantic comedy, this storyline does give Downey Jr. the opportunity to show that Jack has accepted responsibilities. Given how genuinely obnoxious he was in the film’s earlier scenes, this was a necessary trait to define.

Was Robert Downey Jr. Part of the Brat Pack?

While he isn’t always associated with the original members of the group, Downey Jr. co-starred in many Brat Pack-adjacent projects in the late 1980s. He would go on to star with James Spader in the Brett Easton Ellis adaptation Less Than Zero, and appeared alongside Anthony Michael Hall in both Weird Science and Johnny Be Good before joining the cast of Saturday Night Live, where he was fired after just one season. In the aftermath, Downey Jr. would refocus his career on more serious projects, and earned an Academy Award nomination for Best Actor for his performance in the biopic Chaplin.

While many “Brat Pack” members struggled to find interesting roles in the immediate aftermath of their initial stardom, Downey Jr. had one of the greatest comebacks in cinematic history. Although personal struggles cut him out of Hollywood for a time, Downey Jr. managed to become the biggest star on the planet after kick-starting the MCU with 2008’s Iron Man. While he is now an Academy Award winner for Oppenheimer, being in the Brat Pack is still an important part of his legacy.

The Pick-up Artist is currently not available to stream in the U.S.