- Acceptable Targets: The film is about Irish mobsters who seem to run the whole town.
- Adaptation Displacement: Many people don't even know the film is based on a graphic novel.
- Award Snub: Following its release, the film was an early favorite to win big at that year's Oscars. In the end, it won only won one Oscar — a posthumous Best Cinematography award for Conrad Hall, who passed away in-between the film's release and the Oscar nominations being made — with all its other nominations being in the technical categories. That being said, its snubs weren't seen as a massive injustice, so much as the result of it being released too early in a year with one of the most incredibly competitive Oscar races in history.
- Awesome Music: Thomas Newman's haunting, gorgeous score is at least as beautiful as Conrad Hall's luscious cinematography.
- Complete Monster:
- Original comic, by Max Allan Collins: Connor Looney is well known as a bloodthirsty paranoiac who serves as a hitman for his father. After initiating an unnecessary bloodbath, Connor becomes obsessed with Michael O'Sullivan's young son having been a witness, and later heads to the O'Sullivan home after setting Michael himself up for death, murdering Michael's wife and younger son. Connor is later revealed as a pedophile who frequents and beats child prostitutes, showing a disdain for any moral standard. Upon growing sick of his protection, Connor murders an ally of Michael's and kidnaps the man's wife, intending to murder her when Michael is lured out.
- Film novelization, by Max Allan Collins: Harlen Maguire is a death-loving hitman who spends his free time photographing murders, many of which he himself perpetrates. Introduced killing a wounded man in a street alley, Maguire is then hired to track down Michael O'Sullivan and his son, Michael Jr., happily hoping to murder them both and add them to his massive "gallery of death". Slaughtering an entire cafe, murdering one of his own partners, and killing an innocent couple along the way, Maguire mortally wounds O'Sullivan and attempts to photograph his dying moments before moving onto Michael Jr., even after the contract on the duo has been called off.
- Magnificent Bastard:
- Original comic, by Max Allan Collins: Michael O'Sullivan is a war hero turned hitman for John Looney, known as the "Angel of Death", who is betrayed by the paranoid, bloodthirsty Connor Looney and his family killed except for his son Michael Jr. Targeting mob banks and stealing their money to weaken the Capones, Michael teals the Looney ledger to give it to Elliot Ness and his Untouchables to remove Looney from power and weaken the Capone outfit to the point they give him Connor. Repeatedly a step ahead of pursuers until the end, Michael wages an effective war against the most powerful mob in the country with only his son, skills and cunning.
- 2002 film: Michael Sullivan is a hitman in service of John Rooney. One of the most feared in the business who maintains a love for his family, Sullivan is betrayed by his boss's son Connor who sets him up for death and murders his wife Annie and son Peter. Alongside his surviving child Michael Jr., Sullivan goes on the run and seeks to erode the Rooney relationship with the Capones by targeting mob banks and stealing their money. Staying ahead of the Capones and Rooney killers alike, Sullivan eventually targets John Rooney directly, knowing his death will revoke Connor's protection permanently.
- Moral Event Horizon: Connor crosses it when he murders Michael Sr.'s wife and younger son, mistaking him for his older brother, just because he thinks the boy will rat him out.
- Nightmare Fuel:
- Connor's murder of Annie and Peter. Adult Fear at its finest. The music doesn't make things better, particularly when Connor enters the room. Murder in Four Parts. Blow-by-blow account: Michael Sr. frantically tries to call home, but the phone is off the hook. The camera cuts to Annie drying Peter off after a bath, then again to the upstairs hall. The bathroom door opens, and Connor enters, wearing a long coat and fedora, drawing a gun on mother and son. The camera moves back and forth between the pistol and Connor's eyes as Annie screams, then outside as Michael Jr. arrives home and sees two flashes inside his house, along with two gunshots. Getting off his bike, Michael Jr. sprints to the door... just as Connor reaches it. Michael Jr. freezes to the spot as Connor removes his hat and straightens his hair. Without seeing Michael, he opens the door, takes a swig from a flask, and leaves.
- Maguire's introduction, with him coldly finishing off a dying victim while an incredibly creepy Dixieland number plays in the background.
- Signature Scene: The haunting shootout at the end, where the elder Sullivan guns down Rooney and his men with only four words shared between them.
- Tear Jerker: Who doesn't feel sorry for a little boy who's just lost his mom and little brother and is on the run from hitmen aiming to kill him and his father?
- John Rooney's role in the end serves as this. He knows already that his son has been embezzling from him for years and it's hinted that Michael was closer family to him than Connor ever could be. However, despite realizing that Connor's death is imminent, he refuses to give him up, instead imploring for Michael to leave with his own son while he can. When Michael eventually returns to kill Rooney (as well as his entire entourage), the old man can only solemnly remark that he's glad that Michael would be the one to kill him.
- The film was the final film appearance of Paul Newman (not including his voice-only acting which came after), making this a Meta Tear-Jerker in Hindsight.
YMMV / Road to Perdition