Yes. Matt Damon and Gwyneth Paltrow starred together in Contagion and in The Talented Mr. Ripley.
The three starred together in The Good Shepherd (2006).
Matt Damon played cards in Rounders.
The two haven't appeared in any movie together. Well, not yet, anyway.
Pepper Polts
Yes
The Royal Tenenbaums Also starring Gene Hackman, Gwyneth Paltrow, Angelica Huston
This plot summary fits The Talented Mr. Ripley, released in 1999, directed by Anthony Minghella, and starring Matt Damon, Jude Law, and Gwyneth Paltrow.
Gwenyth Paltrow received the Best Actress Oscar for Shakespeare in Love
Gwyneth Paltrow
Duets
The three starred together in The Good Shepherd (2006).
No, Damon did not end up marrying Terry by the end of 'Soul Food'. In the movie, Terry left town to pursue her career, and Damon got back together with his ex-girlfriend Bird.
Matt Damon played cards in Rounders.
The two haven't appeared in any movie together. Well, not yet, anyway.
Matt Damon
Pepper Polts
DAMON? As in Matt Damon.