Latest Photos 'Friends' Creator Reveals Why Brad Pitt Was 'Hesitant' To Guest Star Opposite Jennifer Aniston Brad Pitt received an Emmy nomination for his guest appearance on Brad played the actress' boyfriend Randy on four episodes of Dallas between 1987 and 1988 and was rumored to have romanced her off-camera as well. But in 1989, when she was 17, McCall married He appeared in a memorable episode of "Friends," which celebrates its 25th anniversary this month, in 2001, when he was married to Jennifer Aniston, aka Rachel Green. At the time, Pitt portrayed Jennifer Aniston revealed her favorite episode from Friends It's not easy to keep a show on a winning run for ten years without sacrificing the plot, but Friends did it seamlessly. There The couple were married from 2000-2005. Pitt appeared on Friends in 2001 as a former classmate of Aniston's character Rachel Green in the season eight episode "The One With the Rumour". This was the only time that Brad Pitt and Jennifer Aniston acted together during their marriage. Entertainment Weekly reported that Brad Pitt would appear on the series in flashback scenes wearing a fat suit, though the scenes were never filmed and the episode only refers to his past obesity. In this Season 8 episode, Aniston's then-husband, Brad Pitt, appears as a guest star. He plays Will, an old friend of Ross' who comes to Thanksgiving, and turns out to hold a grudge against spe7.