Sean Penn in the context of "Like a Prayer (album)"

True Blue is the third studio album by American singer-songwriter Madonna, released on June 30, 1986, by Sire Records. In early 1985, Madonna became romantically involved with actor Sean Penn, and married him six months later on her 27th birthday. Additionally, she met producer Patrick Leonard while on the Virgin Tour, and formed a professional relationship with him. The first songs they created together were "Love Makes the World Go Round", and the ballad "Live to Tell," which was featured in the film At Close Range, in which Penn starred.

In late 1985, Madonna and Leonard began working on her third studio album; she also enlisted the help of former boyfriend Stephen Bray, with whom she had worked on her previous record Like a Virgin (1984). Titled True Blue, the record saw Madonna co-writing and co-producing for the first time in her career. Inspired by Madonna's love for Penn, to whom she dedicated it, True Blue is a dance-pop album that features influences of Motown sound, girl groups, and Latin pop.

Carlito's Way is a 1993 American crime drama film directed by Brian De Palma and written by David Koepp, based on the novels Carlito's Way (1975) and After Hours (1979) by Judge Edwin Torres. It stars Al Pacino, Sean Penn, Penelope Ann Miller, Luis Guzman, John Leguizamo, Jorge Porcel, Joseph Siravo and Viggo Mortensen.

Pacino portrays Carlito Brigante, a Nuyorican criminal who vows to go straight and to retire in Paradise. However, his criminal past proves difficult to escape, and he is unwillingly dragged into the same activities that got him imprisoned in the first place. The film is based mainly on After Hours, but it used the title of the first novel to avoid it being confused with Martin Scorsese's 1985 film. This is the second film collaboration with Pacino and De Palma, after Scarface (1983).

I Am Sam (stylized in all lowercase) is a 2001 American drama film co-written and directed by Jessie Nelson. It stars Sean Penn, Michelle Pfeiffer, Dianne Wiest, Dakota Fanning, Richard Schiff, Loretta Devine and Laura Dern.

Nelson and co-writer Kristine Johnson researched the problems facing adults with intellectual disabilities by visiting the non-profit organization L.A. GOAL (Greater Opportunities for the Advanced Living). They subsequently cast two actors with disabilities, Brad Silverman and Joe Rosenberg, in key roles. The film's title is derived from the lines "I am Sam / Sam I am" of the book Green Eggs and Ham by Dr. Seuss, which is included in the movie.

The Thin Red Line is a 1998 American epic war film written and directed by Terrence Malick. It is the second film adaptation of the 1962 novel by James Jones, following the 1964 film. Telling a fictionalized version of the Battle of Mount Austen, which was part of the Guadalcanal campaign in the Pacific Theater of the Second World War, it portrays U.S. soldiers of C Company, 1st Battalion, 27th Infantry Regiment, 25th Infantry Division, played by Sean Penn, Jim Caviezel, Nick Nolte, Elias Koteas, and Ben Chaplin. The novel's title alludes to a line from Rudyard Kipling's poem "Tommy", from Barrack-Room Ballads, in which he says British foot soldiers are called a "thin red line of [h]eroes", referring to the stand of the 93rd Regiment in the Battle of Balaclava of the Crimean War.

The film marked Malick's return to filmmaking after a 20-year absence. It co-stars Adrien Brody, George Clooney, John Cusack, Woody Harrelson, Jared Leto, John C. Reilly, and John Travolta. Reportedly, the first assembled cut took seven months to edit and ran five hours. By the final cut, footage of performances by Bill Pullman, Lukas Haas, and Mickey Rourke had been removed (one of Rourke's scenes was included in the special features outtakes of the Criterion Blu-ray and DVD release). The film was scored by Hans Zimmer and shot by John Toll. Principal photography took place in Queensland, Australia and in the Solomon Islands.

Mystic River is a 2003 American neo-noir mystery drama film, directed and co-produced by Clint Eastwood, and starring Sean Penn, Tim Robbins, Kevin Bacon, Laurence Fishburne, Marcia Gay Harden, and Laura Linney. The screenplay, written by Brian Helgeland, was based on the 2001 novel by Dennis Lehane. It is the first film in which Eastwood was credited as composer of the score.

The film was produced by Village Roadshow Pictures, Malpaso Productions and NPV Entertainment, premiered at the 2003 Cannes Film Festival on May 23, 2003, and was released on October 15, 2003 by Warner Bros. Pictures, and was a critical and commercial success. Mystic River was nominated for six awards at the 76th Academy Awards, including Best Picture, winning Best Actor for Penn, and Best Supporting Actor for Robbins.