Mystic River

Penn's portrayal of a hardened Irish-American gangster who lives by an old school criminal code had everything. The tough guy hardened crim, the committed family man, the loyal friend, the vengeful force. This scene where Jimmy Markum sits out the wake of his murdered daughter on the porch is joined by his friend and potential suspect Dave Boyle (Tim Robbins).  Jimmy offers a glimpse of the struggle between his tortured grief and the hardening resolve for vengeance in this moving monologue. Not over cooked, not underdone, just right. Very, very difficult to do. An Oscar-winning performance

Dead Man Walking

Penn plays Matthew Poncelet a convicted murderer on death row, Susan Sarandon is the nun who befriends him and take personal interest in his spiritual redemption. This is the climax to a very good film that is a moving and intimate portrait of a man getting ready to meet his maker.

 

Milk

Penn's other Oscar winning role was that of Harvey Milk the first openly gay man elected to public office in America and who was gunned down by colleague Dan White in 1978. The speech very cleverly reveals the particular political skill that Harvey Milk had in taming a charged crowd and bending the situation to his political will. Every political speech made by Penn in the film represents a progression in his development as a politician and as a man. This is the speech where Milk is completely in control, both of the political situation and seemingly, his own destiny.

She's so Lovely

Penn won Best Actor at 1997 Cannes Festival for his portrayal of a chaotic yet charismatic former mental patient who goes to compete for his ex-wife's affections with her current husband.  Written by Hollywood legend John Cassavetes and directed by his son Nick, it's a quirky film imbued with bittersweet charm and the darker side of romance, no wonder the French loved it. A rare on screen duet with his then wife Robin Wright-Penn.

   

21 Grams

An understated yet decidedly brilliant film. Penn's monologue, probably asks more questions than it answers in the final scene, however that can only add to a film that begs the biggest of all questions yet is never pretentious or patronising.

At Close Range

Yes, we said five, but this is not a monologue as such but an intensely brilliant scene with scary Christopher Walkin and a very young but able actor – Penn in the final scene. The film was based on the real life suburban Pennsylvania crime family led by Bruce Johnston Sr. Not his break-through role but one that catapulted him into the A-list. Allegedly, at the last minute Penn swapped the dummy gun for another with real blanks, which can do damage at close range, just before the cameras started rolling, so Walkin's expression is one of genuine terror.