![Tom Cruise at Sean Penn's Bachelor Party August 14, 1985 Credit: Ralph Dominguez/MediaPunch Stock Photo - Alamy Tom Cruise at Sean Penn's Bachelor Party August 14, 1985 Credit: Ralph Dominguez/MediaPunch Stock Photo - Alamy](https://c8.alamy.com/comp/2F4W53X/tom-cruise-at-sean-penns-bachelor-party-august-14-1985-credit-ralph-dominguezmediapunch-2F4W53X.jpg)
Tom Cruise at Sean Penn's Bachelor Party August 14, 1985 Credit: Ralph Dominguez/MediaPunch Stock Photo - Alamy
![Cher Opens Up About Her Famous Past Lovers, Including Tom Cruise and Val Kilmer | Entertainment Tonight Cher Opens Up About Her Famous Past Lovers, Including Tom Cruise and Val Kilmer | Entertainment Tonight](https://www.etonline.com/sites/default/files/images/2018-09/tom-cruise-cher-gettyimages-78799956.jpg)
Cher Opens Up About Her Famous Past Lovers, Including Tom Cruise and Val Kilmer | Entertainment Tonight
![Carey O'Donnell on Twitter: "Here's a pic of Steve Rubell, Andy Warhol, Keith Haring and Tom Cruise at Madonna & Sean Penn's wedding https://t.co/t4Nd5YYsuu" / Twitter Carey O'Donnell on Twitter: "Here's a pic of Steve Rubell, Andy Warhol, Keith Haring and Tom Cruise at Madonna & Sean Penn's wedding https://t.co/t4Nd5YYsuu" / Twitter](https://pbs.twimg.com/media/DWstugnU0AIymjF.jpg)
Carey O'Donnell on Twitter: "Here's a pic of Steve Rubell, Andy Warhol, Keith Haring and Tom Cruise at Madonna & Sean Penn's wedding https://t.co/t4Nd5YYsuu" / Twitter
![My Wild Summer With Tom Cruise: Women, Sean Penn and the Making of 'Risky Business' – The Hollywood Reporter My Wild Summer With Tom Cruise: Women, Sean Penn and the Making of 'Risky Business' – The Hollywood Reporter](https://www.hollywoodreporter.com/wp-content/uploads/2017/06/gettyimages-74704314_-_embed_2017.jpg?w=771)
My Wild Summer With Tom Cruise: Women, Sean Penn and the Making of 'Risky Business' – The Hollywood Reporter
![Sean Penn lets rip, Mick Jagger flips the bird, and Tom and Nicole go to the Oscars – The Irish Times Sean Penn lets rip, Mick Jagger flips the bird, and Tom and Nicole go to the Oscars – The Irish Times](https://www.irishtimes.com/resizer/TOwawIIgYkM9m-VgZ3lkbNy3h5E=/arc-photo-irishtimes/eu-central-1-prod/public/K3LC47M4IZCPDMQBG2CFTRKSFQ.jpg)
Sean Penn lets rip, Mick Jagger flips the bird, and Tom and Nicole go to the Oscars – The Irish Times
![Fast Times" and "Risky Business" created the '80s: How these iconic teen films led the way to "Heathers" and John Hughes | Salon.com Fast Times" and "Risky Business" created the '80s: How these iconic teen films led the way to "Heathers" and John Hughes | Salon.com](https://mediaproxy.salon.com/width/1200/https://media.salon.com/2014/06/fast_times_heathers_risky.jpg)