• 1990 Film debut, "The Ages of Lulu", directed by Bigas Luna
• 1991 Co-starred in Pedro Almodovar's "High Heels"
• 1992 Reteamed with direcor Luna for "Jamon, Jamon"
• 1993 Portrayed an oversexed man in Luna's "Golden Balls/Huevos de Oro"
• 1994 Delivered change of pace turns in "The Detective and Death/El Detective y la Muerte" and "Numbered Days/Dias Contados"
• 1995 Starred in "Mouth to Mouth/Boca a Boca"; released in USA in 1997
• 1997 English-language debut opposite Rosie Perez in "Perdita Durango"
• 1997 Reteamed with Almodovar for "Live Flesh"
• 1999 Served as executive producer and star of "Los Lobos de Washington"
• 2000 Starred as Cuban writer Reinaldo Arenas in "Before Night Falls"; received Best Actor Academy Award nomination
• 2002 Had featured role in "The Dancer Upstairs", directed by John Malkovich; screened at Sundance
• 2003 Co-starred in the award-winning feature "Monday's in the Sun"
• 2004 Appeared opposite Tom Cruise in the thriller "Collateral"
• 2004 Starred in "Mar Adentro/The Sea Inside" about the Life story of Spaniard Ramón Sampedro, who fought a 30-year campaign to win the right to end his life with dignity; received a Golden Globe nomination for Best Lead Actor (Drama)
• 2005 Cast in Andy Garcia's independent film "The Lost City," centered around a club owner in Havana, Cuba, during the 50's
• 2007 Played a lovesick romantic in Mike Newell's adaptation of "Love in the Time of Cholera"
• 2007 Played a murderous drug runner in the Coen brothers' "No Country for Old Men"; earned an Oscar nomination for Best Supporting Actor
• 2007 Played the sinister monk, Brother Lorenzo in Milos Forman's "Goya's Ghosts"