Robert Downey Jr. Doubted His Kissing Skills After Locking Lips With Molly Ringwald

Sometimes, too much advice can be wholly overwhelming. Actor Robert Downey Jr. knows that feeling well. In 1987's "The Pick-Up Artist," Downey Jr. and Molly Ringwald played love interests. Downey Jr.'s character Jack tries his best to be suave — perhaps more so than Downey Jr. himself was when he met his wife, who didn't have a great first impression of him. However, "The Pick-Up Artist" isn't all lovey-dovey. A big part of the plot is that Ringwald's character owes a mobster money. 

The film included enough romance for Downey Jr. and Ringwald to have to kiss as their characters. In a video interview published by W Magazine in 2024, Downey Jr. reminisced about how Ringwald was likely his first onscreen kiss — though he doubted his kissing abilities after getting some feedback from one of the movie's producers.

"I'm gonna say it was probably 'The Pick-Up Artist' with Molly Ringwald," Downey Jr. said, "That I recall. Warren Beatty was on set and he was giving us a lot of direction about the kiss. Like, so much direction that by the time he was done — and he's a supergenius and I've learned so much from him — I wasn't even sure I knew how to kiss."

Despite being thrown for a loop by Warren Beatty's onscreen kiss coaching, Robert Downey Jr. has spoken highly of acting advice he received from the producer. On "The Off Camera Show" in 2013, Downey Jr. reminisced about being on "The Pick-Up Artist" set and Beatty asking what Downey Jr's character Jack was doing. Downey Jr. gave a straightforward answer, and Beatty said it was incorrect. Downey Jr. tried a new answer, "[Beatty] goes, 'No, no. You're trying to get to work. But you keep getting distracted, so your action keeps changing.' ... He goes, 'Nobody is gonna be inspired all the time. But everybody should know what they're doing if they're being paid to play a part in a movie. It's irresponsible not to.'"

Downey Jr. said he thanked Beatty for the advice, and he evidently took it to heart if he remembered it over 20 years later. However, in an E! News interview from 1987 for "The Pick-Up Artist," Downey Jr. also discussed how he learned that actors sometimes receive contradictory advice from different creatives on set. "When you do supporting roles," Downey Jr. said, "you know, you'll see the lead actor in the corner getting really pissed because the producer is saying, 'Smile!' and then the director comes and goes, 'This is the one scene where you shouldn't smile.'"

Years before Robert Downey Jr. and Molly Ringwald shared the screen in "The Pick-Up Artist," she wanted them to star in another movie together. "Pretty in Pink" has iconic fashion moments and romance between Ringwald's character Andie and Andrew McCarthy's Blane. But in the original draft of John Hughes' script, Jon Cryer's Duckie is with whom Andie ends up. The ending was changed due to poor audience reception at a screen test, but Ringwald believes the original friends-to-lovers arc would've worked if an actor she suggested — Downey Jr. — was playing Duckie.

"You Couldn't Ignore Me if You Tried" by Susannah Gora is all about John Hughes' films and describes Ringwald's feelings about that: "She believed Duckie should have been played by 'somebody like Robert Downey, Jr. He was different, and he was quirky, but it was completely imaginable that we would end up together.'" Ringwald made it clear that she wasn't trying to slam Cryer by bringing up how she'd wanted Downey Jr. as his part. 

Gora's book quotes Cryer in a DVD commentary saying, "'Molly dropped the bomb that she would've been fine with the original ending if Robert Downey, Jr., had played Duckie ... but since it was me, she just couldn't see it. It was like, wow, so I'm that unattractive? Thanks, Mol!'" Thankfully, Cryer hasn't joined the list of Downey Jr.'s most famous feuds, and Downey Jr. and Ringwald did eventually get to collaborate.