Lloyd could be a Jerkass Woobie - he travels across the country nearly getting killed/raped in the process just to give his dream girl her briefcase, his best friend steals her from him (so he thinks), and finally learns that she's already married. And to top it off he's simply too dumb and/or crazy to realize that she's completely out of his league anyway.
Which one's "Dumb" and which one's "Dumber"? Lloyd for having even less sense than Harry exhibits, or Harry for letting Lloyd fast-talk him so often?
And You Thought It Would Fail: Bennett Yellin's initial draft of the script was apparently so disjointed that it had gained a negative reputation among film investors. After the script was re-written, it was pitched to producers under the fake title A Power Tool Is Not a Toy, in order to get them to even read it.
Angst? What Angst?: Subverted; after Mental realizes that Harry and Lloyd gave him rat poison instead of his ulcer medication, he manages to choke out "You son of a... bitch!" before dying. Next time we see Harry and Lloyd, they are visibly distraught, Harry especially as the insult that served as Mental's last words was directed at him. Especially telling, it's one of very few times we see Harry and Lloyd taking something seriously.
Mental's death. He's convulsing on the floor with Lloyd and Harry desperately trying to save him, only for them to accidentally kill him with rat poison that they thought were pills. Though he was already trying to kill them beforehand, and his murder of Harry's bird already made him irredeemable.
The death of one of the Icelandic snow owls. Lloyd accidentally killing a highly endangered bird that's one of the last of its species? Tragic. This murder being done with a bottle cork shot like a bullet, complete with a shot of the cork flying towards it and the owl making an Oh, Crap! face? Hilarious. The villains seeing this as some kind of mob-style message in payback for Mental's aforementioned murder of Harry's bird? Even more hilarious.
Lloyd's Indulgent Fantasy Segue, where he sees Mary and her husband having a heartwarming reunion, with Mary being willing to introduce Lloyd to him, with Lloyd going Laughing Mad and murdering him, only for the scene to have just been a fantasy. It comes out of nowhere and feels like the climax to him being strung along for the whole movie, making it absolutely hilarious.
Esoteric Happy Ending: Harry and Lloyd may have helped foil the bad guys (by accident), but they have nothing to show for their adventure. Lloyd Did Not Get the Girl (and was never going to anyway), Harry didn't fare any better, their journey cost them all the money they had, they blew all the cash in the briefcase on frivolous items that were confiscated anyway, they lost their vehicles, and they have no choice but to walk across the country by foot to get back home. While their stupidity allows them to maintain their cheerful demeanors, their situation is much worse at the end of the film than it was at the beginning.
Fanon Discontinuity: Most fans of the original film would prefer to pretend that the prequel never happened.
First Installment Wins: The original Dumb and Dumber is one of the most popular and beloved comedy movies of the 1990's. By contrast, the prequel, Dumb and Dumberer, is often regarded as one of the worst comedies of the 2000's, while Dumb and Dumber To is a Contested Sequel.
Who's "Dumb" and who's "Dumber"? Many people would think it was about the main characters, but who's really the "Dumber" people in the movie here; the idiots, or the villains who believe the idiots are actually competent and intelligent?
If Mary had been single as Lloyd hoped and if they had gotten together, she might have been...Mary Christmas.
Listening to all the sexual innuendos and double entendre from Harry and Lloyd once you learn in the sequel that they know absolutely nothing about sex.
Harry: (referring to a woman) Holy jeez, look at the butt on that!
Lloyd: (assuming that Harry was referring to the man who was seen walking with her) Yeah, he must work out!
Harry and Lloyd staying at a honeymoon motel and sitting in a heart-shaped hot tub, together.
What's funnier is the fact that the two mooks following them thought that they were a couple.
In the unrated version of the film, the dialogue is changed, with the difference being Lloyd letting Harry know that he’d happily bone him if he had a pair of boobs.
The scene where Lloyd is resting on Harry's shoulder as the former sleeps and the latter drives.
The duo sitting on a double bed while enjoying room service and wearing bath robes.
The way Harry holds onto Lloyd while riding the bike.
Lloyd hugging Harry and crying after the latter announces a drive to Aspen, leading Harry to declare, "Okay, that’s enough." after ten seconds or so.
Lloyd, believing that Harry set up a date between him and Mary, hugs and kisses his best friend(?) in response.
At the end of the film, Harry and Lloyd come across a bus full of supermodels who are looking for men to oil them up. Harry and Lloyd, being the dimwits that they are, turn down the offer. After that, they play a friendly game of tag while walking off, together.
Nicholas ordering Mary's husband's kidnapping for her heirloom, then shooting Harry without any second thoughts.
Mental murdering Harry's parakeet just to give him a message. Tellingly, he's the only one of the villains who actually dies.
Presumed Flop: For as much as it was comprehensively mauled by critics and made far less money than the films either side of it, Dumb and Dumberer did actually succeed in making back twice its budget.
Sequelitis: The Farrely brothers had nothing to do with either Dumb and Dumberer (not to be confused with Dumb and Dumber To, which had The Farrelly brothers involved), or the short-lived animated TV series. Mediocrity ensues.
"Wanna hear the most annoying sound in the world?"
Special Effects Failure: The "Icelandic snow owls" are definitely just puppets. Admittedly, this makes the scene where Lloyd accidentally kills one with a bottle cork much easier to laugh at, since having a realistic owl would make the scene a lot less palatable.
In the prequel it's quite obvious in several instances that Lloyd's chipped tooth is just covered in black makeup.
When Lloyd drives himself and Harry in the wrong direction for five hours, Harry reaches a Rage Breaking Point that they're now stuck in the middle of nowhere with nothing. There's no way for them go get to Aspen, get home, or even eat and sleep. Harry then decides "Screw This, I'm Outta Here" and starts walking home, simply because he's so mad at Lloyd.
Lloyd: I'm only human, Harry! Anybody can make a mistake. Come on, stop being a baby! So we backtracked a tad!
Harry: A tad! A tad, Lloyd! You drove almost a sixth of the way across the country in the wrong direction! Now we don't have enough money to get to Aspen, we don't have enough money to get home, we don't have enough money to eat, we don't have enough money to sleep!
Lloyd: Well, it's not gonna do us any good to sit here whining about it. We're in a hole! We're just gonna have to dig ourselves out.
Harry: Okay, all right, you're right, you're absolutely right, Lloyd.
Lloyd: Where ya goin'?
Harry: Home! I'm walking home!
Lloyd: Oh, well, pardon me, Mr. PERFECT! I guess I forgot that you never, ever make a mistake!
They Changed It, Now It Sucks!: The unrated cut is often regarded as less funny than the theatrical version, because numerous gags that previously worked just fine with sharp editing have now been stretched out to the point that they become a lot more awkward and off-putting, and the jokes added back in are just plain awkward and off-putting, having been cut the first time for a good reason.
The only aspect of Dumb and Dumberer to be consistently praised was Eric Christian Olsen's performance as the young Lloyd, with most critics finding him perfectly believable as a younger version of Jim Carrey.
Also from the same movie is Bob Saget's scene where he absolutely loses his shit when he thinks Harry has covered every inch of his bathroom in excrement. In the hands of someone lesser it would have been a fairly unremarkable moment, but Saget's utter commitment to the bit elevates it to being just about the only unambiguously funny moment in the entire movie.
Unintentional Period Piece: Try to imagine how well Lloyd storming through airport security would work in a post-9/11 world.
The Woobie: Petey the parakeet, who Mental rips the head off of just to scare Harry and Lloyd.
