Sean Penn has owed Winona Ryder $500 for four decades: “I’m waiting to collect”
If you type the words ‘Sean Penn’, ‘Winona Ryder’, and ‘friends’ into Google, you’ll be met with a million results about how both guest-starred on a certain iconic sitcom at different points. Remember Penn as Phoebe’s sweaty boyfriend, or Ryder as Rachel’s sorority sister who could never forget their drunken smooch? Good times.
Ultimately, though, these results are pointless and mostly just a fun excuse to mention Friends. What we’re really looking for with such a search is confirmation that Penn and Ryder are pals in real life, and that’s harder to come by. However, judging by Ryder’s insistence that Penn has owed her 500 bucks for the last two decades and counting, it stands to reason that they were friendly at some point in the past.
By the time Ryder broke through as a teen superstar with roles in Beetlejuice and Heathers at the end of the 1980s, Penn – a decade older, if not a decade wiser – had already been one of Hollywood’s brightest hopes since 1981. After catching the eye as the beloved stoner Jeff Spicoli in Fast Times at Ridgemont High, he quickly became one of the industry’s most intense and driven young stars.
Leading roles in the spy thriller The Falcon and the Snowman, the neo-noir At Close Range, and the LA cop drama Colours cemented his status as arguably the best leading man of his age group. However, by the time the ‘80s transitioned into the ‘90s, his off-screen antics and the pressures of fame left him feeling burned out on acting. So, he switched his focus to directing, helming music videos for country stars Shania Twain and Lyle Lovett, as well as his feature-film debut.
Fascinatingly, The Indian Runner, a crime drama set in ‘60s Nebraska, cast Viggo Mortensen and David Morse as two brothers on a collision course, one a deputy sheriff and the other a criminal. It was inspired by the Bruce Springsteen song ‘Highway Patrolman’, from the seminal Nebraska album, and was a real passion project for Penn, who had been trying for almost a decade to bring the song to the big screen.
At this point, Penn must have been excited about the creative possibilities of directing and felt acting was a thing of the past, because Ryder remembered having a conversation with him one day not long after he completed the film. “I remember when I was about 18,” she revealed to Elle, “Sean Penn made a bet with me. He had just directed his first movie, and he’s like, ‘By the time you’re 30, I will bet you $500 that you’ll be sick of acting.’”
At this point, Ryder had barely started in the industry, comparatively speaking, but had already starred in several hits and been nominated for Golden Globes and Independent Spirit Awards. To her, acting was still the most exciting thing in the world, so she decided to call Penn’s bluff and take him up on the bet. Fast forward 12 years, and the 30-year-old hadn’t become bored with acting – but Penn was nowhere to be seen with her $500. “I’m still waiting to collect,” she grinned, clearly aware she’d never actually get her hands on those 500 big ones.
To play devil’s advocate, though, Penn may have been closer to the truth than Ryder wants to admit. You see, in 2001, at the age of – you guessed it – 30, she was famously arrested for shoplifting $5,500 of designer clothing from Saks Fifth Avenue in Beverly Hills. She was placed on trial, with few observers able to comprehend why a rich and famous actor would feel the need to steal, and was sentenced to three years of supervised probation, during which she took a hiatus from acting.
Later, when asked why she did something so baffling, Ryder told Porter magazine, “Psychologically, I must have been at a place where I just wanted to stop…It allowed me time that I really needed, where I went back to San Francisco…I just had other interests, frankly.” I don’t know about you, but that explanation certainly seems to hint at someone who had grown sick of acting. If anything, it sounds like Ryder owes Penn 500 bucks! Pay up, Winona.
