- I just don't get it! She seems totally uninterested in me, despite my smothering obsessiveness!
- Paps, you've been like the drunken, abusive grandfather I never had.
- We should call this place Wackyville... because it's wacky!
Old salt in fishing village
- When you're on the Queen Catherine, don't let 'em give you any of that flank steak bullshit. You know what I mean? Try the London Broil.
- Gosh you're cute. Wanna buy a monkey?
- Man, oh man, I hate those fancy lads!
- Trina: Thats wonderful. I'm always flattered when a psychotic becomes smitten with me.
- Cupcake: Now I know what you're thinking. "What could be stranger than a big fatass floatin' cupcake?" Heh. How about one that spits tobacco?
- Kenny: Mmmm. Gum.
- Paps: Okay, you icy bastard, how about a hot cup-a joe!
- Nathanial: Paps, you've been like the drunken, abusive grandfather I never had.
- Paps: Ah, stop that. You'll have my glass eye foggin' over.
- Nathanial: Oh, cappy, tell me about all of this. Tell me about the sea. What does it mean to you?
- Captain Greybar: Basically, money. I come from six generations of seamen all with the same goal in life: catch fish, sell 'em, get drunk, and get laid.
- Nathanial: I love sitting up here, looking at those bright, twinkly things in the sky, I forget their technical name.
- Trina: Stars.
- Nathanial: Whatever.
- Nathanial: I overheard the captain saying it would be jolly-jack splendid to spend a fortnight or two in Hawaii
- Kenny: Yea... that sounds like the captain... you do good impressions.
- Skunk: We're just here to catch fish and stink.
- Paps: Mostly the latter.
- Trina: And secondly, don't ever call me missy again or you'll end up losing the rest of your teeth.
- Paps: Sassy little thang ain't she? Want me to give her a SPANKING?
- Skunk: Why doesn't she give ME a spanking?
- He's sailing high on the high seas, without a rudder, a compass, or a clue.
- Chris Elliott — Nathanial Mayweather
- Ritch Brinkley — Captain Greybar
- James Gammon — Paps
- Ricki Lake — Figurehead
- Brian Doyle-Murray — Skunk
- David Letterman — Old salt in fishing village
- Brion James — Big Teddy
- Melora Walters — Trina
- I.M. Hobson — Headmaster Timmons
- Alex Nevil — Thomas
- David H. Sterry — Lance
- Bob Elliott — William Mayweather
- Edward Flotard — Limo Driver
- Jim Cummings — Cupcake (voice)
- Ann Magnuson — Calli
- Russ Tamblyn — Chocki