A season 2 episode of Friends features a storyline where the group makes a list of five celebrities they’re allowed to sleep with while in a relationship, and some listed celebrities end up actually appearing on the show. Friends was one of the biggest shows in the world during its 10-season run from 1994-2004, which made it a frequent stop for some of the biggest celebrities of the era. Some big-name guest stars from Friends include Brad Pitt, Julia Roberts, Reese Witherspoon, Bruce Willis, and Danny DeVito.
The end of the season 2 episode “The One With Frank Jr” makes the freebie list a non-hypothetical situation when Isabella Rossellini, who Ross removed from his list because she was “too international,” walks into Central Perk. The Swedish daughter of Ingrid Bergman enters to the amazement of the gang, with Ross instantly regretting he removed her. Rachel tells him that he’s welcome to try to flirt with her and they’ll call her an “alternate,” so he goes up and tells her he’s allowed to sleep with her. The comment surprises Rossellini, who gives an excellent comeback to Ross while rejecting him.
The Ross-Isabella Rossellini revelation makes one believe this is how most of the Friends characters and celebrities' interactions would go, except maybe Rachel who scored a date with Jean-Claude Van Damme. Out of the 16 celebrities featured on Chandler, Rachel, and Ross's lists, a few of them actually appeared on the series. However, besides Rossellini, almost every time another freebie celebrity comes onto the show they play a fictional character instead of themselves. Here’s a breakdown of each freebie list celebrity that ended up actually guest-starring on Friends.
Susan Sarandon
One of Ross’s possible celebrity freebies was actress Susan Sarandon, who would later appear as Cecilia Monroe in the season 7 episode “The One with Joey’s New Brain.” When Ross listed her, Chandler responded by stating she would be too political and would likely make him donate to charity before sleeping with her, referring to Sarandon’s renowned philanthropic efforts. Considering Sarandon was much older than the cast and was at a high point in her career during Friends, it’s unlikely Ross would have actually been able to flirt with her enough to take her home.
Sarandon’s one-episode Friends role was a part of the main plotline featuring Joey returning to the Soap Opera Days Of Our Lives where he is taking over Sarandon’s character’s character who is killed on the show. Sarandon’s role is as a famous Soap Opera actress who is supposedly one of the best in the business and is famous for slapping people. Her character goes through a crisis when she is killed off, though ends up training Joey for the role and sleeps with him in the process. Sarandon’s real-life daughter Eva Amurri also played a small role in the episode as one of the actresses on Days Of Our Lives.
Kathleen Turner (Jessica Rabbit)
Interestingly enough, one celebrity on Chandler’s list was Who Framed Roger Rabbit's Jessica Rabbit. He claims he included her because he wants to see if he could “make her eyes pop out” like in the movie. On the other hand, the famous actress who voices Jessica Rabbit is Kathleen Turner, who eventually has a recurring role in Friends seasons 7 and 8 as Chandler’s father, Charles “Helena Handbasket” Bing. Considering Chandler lists a fictional character as a freebie, there’s no possible way an interaction could've come to fruition.
Kathleen Turner appears as Chandler’s mysterious father, who he describes as being gay and eventually running his own all-gay burlesque show “Viva Las Gaygas.” It’s suggested in the series that Chandler’s father engaged in dressing drag, but not that he actually transitioned into a woman. Using Kathleen Turner as the actress is something that wouldn’t pass today considering they were playing on Chandler’s father becoming more feminine while also playing on Turner’s infamously deep voice, and used a cis-woman to play the role of a trans-woman.
Winona Ryder
Featured on the final, laminated list of Ross’s freebie celebrities is Winona Ryder, who eventually performs a Friends guest role as Melissa Warburton in season 7. Winona Ryder was one of the most famous actresses of the 1990s and had just recently achieved back-to-back Oscar nominations for Best Actress and Best Supporting Actress when Ross lists her as a woman he can sleep with, so it’s unlikely she would have frequented the same places as him to meet up. Ryder was also in a relationship at the time the episode aired, so Ross’s attempt to woo her likely would have gone the same way that it did with Isabella Rosselini.
Winona Ryder appears in Friends' season 7 episode “The One With Rachel’s Big Kiss” as Rachel’s sorority sister from college, who Rachel tells Phoebe she shared a drunken kiss with at a party. Rachel describes her kiss with Ryder’s character as the wildest thing she’s ever done, so she brings it up to Melissa, who denies it. Rachel kisses Melissa again after dinner to prove to Phoebe it did happen, whereafter Melissa confesses she did remember the kiss and has been in love with Rachel ever since.
Sting
The Police lead singer Gordon “Sting” Sumner is one of the five famous people Rachel eagerly places on her list. While Sting himself doesn’t actually appear on the episode, he is the subject of Phoebe’s plotline in the season 8 episode “The One With Monica’s Boots.” Sting is performing a concert in New York City, so Phoebe tries to track down Sting for free tickets through Ross’s son Ben. Ross reveals that Ben is in the same class as Sting’s fictional son Jack, who happens to be the boy he fights with at school. Phoebe pretends to be Ben’s mom to supposedly meet with Sting about Jack and Ben’s behavior, though ends up only speaking with Sting’s real-life wife Trudie Styler. Sting’s wife realizes Phoebe is just trying to get tickets, so promptly kicks her out of her house. Since Sting was already married with kids at the time of his inclusion on Friends’ freebie lists, it’s unlikely he would have abandoned Styler for a tryst.