1 - Guybrush, about his homemade compass, Part 4 of CMI.
2 - Edward Van Helgen, to Guybrush, about the banjo duel, Part 2 of CMI
3 - Fester Shinetop, sortof to Guybrush, before throwing him underwater, Part 1 of SMI
4 - Wally, to Guybrush, while trapped in LeChuck's Fortress? Part 3 of MI2:LR
5 - LeChuck, presumably to himself, a cutscene during Part 2 of CMI // EDIT: NO WAIT it was Part 4 I meant.

6 - Guybrush, about the rubber chicken with a pulley in the middle, Part 1 of SMI
7 - Pegnose Pete, to Inspector Canard and Guybrush about Guybrush, in a cutscene late in Act 2
8 - ... er, no idea. EDIT: Stan, after being released from the coffin, Part 4 of CMI
9 - Guybrush, about his journey back from Monkey Island, at the beginning of the Final Part of SMI.
10 - Guybrush to Griswald Goodsoup, about his death. Part 4 of CMI.
11 - Dunno. EDIT: Um, is this from when Guybrush digs up Largo's grandfather's grave? I don't know the scene very well.
12 - The Voodoo Lady to Guybrush, after he can't recognise her, Part 2 of CMI
13 - Mr Fossey to his monkey crew, about Guybrush boarding their ship, Part 2 of CMI
14 - Guybrush after being ejected from the snake in Part 2 of CMI
15 - Guybrush to the librarian on Phatt Island, lying about his age, in Part 2 of MI2:LR
16 - No idea! xD EDIT: I think this is Guybrush talking to the Troll in Part 1 of SMI.
17 - The Voodoo Lady, to Guybrush, about who she is, Part 2 of CMI
18 - Dinghy Dog to LeChuck, a cutscene late in Part 4 of CMI
19 - The bartender of the Bloody Lip on Scabb Island, after Guybrush asks him to mix up a Blue Whale, Part 2 of MI2:LR
20 - ... You little cheater! xD EDIT: Oh no, wait, it WAS one of the Fettucini brothers in Part 1 of SMI, while they're insulting each other. I have bad memory. xD
21 - Oh boy, first one that comes to mind is Elaine in the opening cutscene of CMI, but I doubt that's the one you meant.

EDIT: I guess it could also be the gardener on Booty Island to the dog in Part 2 of MI2:LR, though.
22 - I'm gonna guess this is the antique dealer on Booty Island in MI2:LR, but no idea about what.
23 - I know Guybrush says this, but I have no memory of where. I can hear him saying it but can't see anything! D:
24 - Guybrush to Governer Phatt, before being sent to jail for the first time in Part 2 of MI2:LR
25 - Oh come on! xD
26 - This is way too hard. EDIT: Bart says this in the opening cutscene of MI2:LR, after Guybrush finishes telling his story about LeChuck.
27 - And they're very generic.
28 - They could be from anywhere!
29 - You're just teasing us. xD
30 - Guybrush to Elaine, after being caught with her map piece in Part 2 of MI2:LR.
Well, that was fun! How did I do?