Big-Lipped Alligator Moment: There's one part where the Candy Bar Brigade are sitting in a car outside Anna and Hudson's apartment and, apropos of nothing, Butterfinger says "Want me to rape 'em"? Presumably this was an attempt at Black Comedy, but it just seems so out of place and rather out of character for Butterfinger as well. The other bad guys just roll their eyes and tell him to keep reading his picture book, and the whole thing is never brought up again.
Critical Backlash: Hudson Hawk was raked over the coals by critics when it was released. They thought it was an absolutely terrible action movie. Many viewers since have, however, noticed that it is a pretty darn good comedy, which is what its creators intended all along. It has also found an audience among anime fans due to the startling number of parallels to Lupin III.
Fridge Brilliance: Tommy and Hudson know a series of songs's playing times by heart. They sing songs during robberies, not just to time them, but to stay in sync. Songs are sung during the auction house robbery and the Castle Da Vinci assault, but not during the Vatican job, because that one is only done by Hudson — there's no one else to sync with.
Not only that, but their timing and estimates are so perfect, that they inevitably get foiled right after they finish the song.
Fight Scene Failure: At one point when Butterfinger "punches" somebody, his fist clearly goes in front of the person he's "punching". They try to hide this with the camera angle but it's still painfully obvious.
Eddie's quest for a cappuccino becomes highly ironic in an age with a Starbucks on every street corner.
At one point, Kit Kat is trailing Eddie and mimics every movement Eddie makes, including at one point pulling a pair of sunglasses. This was years before Kit Kat's actor David Caruso would make pulling sunglasses a trademark move of his character Horatio Caine in CSI: Miami.
So Bad, It's Good: Those who don't find it an irredeemable mess that mixes bad action, bad comedy and annoying characters, like because aside from actual entertaining moments, they can laugh at how incompetent the thing is.
Spiritual Adaptation: The combination of action and slapstick, the main character being a Gentleman Thief and the overall feel of the film has some people calling it a better live-action Lupin III movie than the actual live-action Lupin III movie.
Squick: The Mario brother who gets stabbed in the face with a rack of syringes. And seems to be almost unfazed by it a couple scenes later, though his partners freak out when they see his face.