Ambiguous Ending: Being one of his (lyrically) darker songs, the music video  for "Party In The CIA" implies that the protagonist is screwed over and ends up in the clutches of some dictator while the lyrics/protagonist say that you "better put your hands up and get in the van or else you'll get blown away." And when the lyrics say that "we only torture the folks we don't like, you're probably gonna be OK," it is not known if that means that the kidnapping is fake, or that the kidnapping is real but the protagonist will receive a painless death.
Critical Dissonance: Running With Scissors was one of his worst-reviewed albums, but contains several fan-favorites.
Al does this to other artists; younger fans might not know that, for instance, "I Lost On Jeopardy" is a cover of Greg Kihn's "Our Love's In Jeopardy". (Kihn wasn't offended—he appears in Al's music video for the song.)
"The Saga Begins" was almost a straight example, with Don McLean once admitting to occasionally singing Al's lyrics by accident during live performances of "American Pie".
"Eat It" has a riff that's so epic the guitar explodes.
Apart from parodying songs that are famous for Epic Riffs themselves ("Smells Like Nirvana," "Beverly Hillbillie / Money for Nothing"), a few of Al's originals fit this trope as well. "I'll Sue Ya," "Dare to be Stupid," and The White Stripes flavored "CNR" all come to mind.
Face of the Band: Al has recorded with the same band (Jon "Bermuda" Schwartz, Jim West, and Steve Jay) for virtually his entire career, and they appear in all his videos.
Lampshaded by the band themselves in "Al's Band," a stand-alone single featuring Al solely on accordion. Sung by the guys themselves, it details their history with him.
By a day. Al released "TMZ" on Alpocalypse on June 21, 2011, which contains the lyrics "... it's getting to the point where a famous person can't / Even get a DUI or go on a racist rant" and "Seems that every single time a star decides to / Shave their head or ram their car into a tree / They're on TMZ." The day before, Ryan Dunn of Jackass had killed himself by getting drunk and plowing into a tree at high speed. The story was, naturally, on TMZ.
The video for "TMZ" depicts a celebrity being plagued by photos of her own behind getting spread everywhere. Scarlett Johansson would go through this for real.
The very first line of "Traffic Jam", "Carbon monoxide making me choke", became far less amusing when 11 years afterward, Al's parents simultaneously succumbed to CO poisoning.
"Canadian Idiot" features the line "Never even bring their guns to the mall". The Toronto mall shooting begs to differ.
"Fat", after learning about how fast food restaurants target and exploit low-income neighborhoods with their cheap but unhealthy food.
"Ringtone" has a line about "folks with Ebola" hating Al's ringtone. This became much less funny after the 2014 Ebola outbreak.
As did "That's Your Horoscope For Today" with the line for Pisces to "try to avoid any Virgos or Leos with the Ebola virus".
"Buckingham Blues" is a satire on the lives of Prince Charles and Princess Diana. Al has not performed or rerecorded this song since the latter's death in 1997.
One of the items mentioned in "Ebay" is a Dukes Of Hazzard ashtray. With the controversy surrounding the Confederate flag, that will now raise some eyebrows instead.
In "Word Crimes", the lyric, "You should never / Write words using numbers, / Unless you're seven, / Or your name is Prince", is starting to feel a little less funny and more like a tribute now that The Artist Formerly Known as Prince has passed away at 57.
A small one: on "Pancreas," he declares that his spleen "just doesn't matter." Ten years after that song was released, he'd play a character on Bojack Horseman who comes dangerously close to dying of a twisted spleen.
"I'll Be Mellow When I'm Dead", off his first album, contains the lyrics "I'd rather have a Big Mac or a Jumbo Jack than all the bean sprouts in Japan!" and "Don't want no part of that vegetarian scene." Al has since become a vegan.
He once wrote a song called "I Lost on Jeopardy". Later, he went on Rock & Roll Jeopardy!...and lost.
Al also won a game of Wheel of Fortune during a charity week, but lost on the "Friday Finals" tournament at the end of the week.
"Theme from Rocky XIII" depicted the Champ taking ownership of the neighborhood deli...this was before Rocky Balboa, wherein he purchased a restaurant.
Also, in "It's All About the Pentiums", Al describes his personal computer as having a 40-inch-wide flatscreen monitor, 100 gigabytes of RAM, and a 32-bit operating system which is connected to the internet via a T1 line. While 40 inch monitors did exist and in fact became common a few years later as High Definition became standard, 32-bit x86 processors (Pentiums) cannot address more than 64 gigabytes of RAM, and no commercial 32-bit operating system as of 1999 permitted addressing more than 4. However, some versions of the 64-bit Windows 7 (and now Windows 8) can address 192 gigabytes of RAM thus making the lyrics of his song a possibility. As of now, most commercial motherboards can only support between 32-64 gigabytes of RAM. A dedicated RAM disk, on the other hand...
In the same song, Al says, "You could back up your whole hard drive on a floppy diskette." While small floppy diskettes can actually store up to over 200 megabytes of RAM, they were actually superseded through the years up from 1999 by data storage methods such as USB flash drives, which could now contain up to a terabyte; these drives were in their stages of infancy in 1999 at the time that the song was released, and did not go into the first commercial product until over a year later.
Also, not withstanding, that with the advance of this technology, it has since become common practice for one to back up their entire hard drive so they don't lose any of their files in the event of their computer becoming unusable.
The video for "Ringtone", produced by the minds behind Supernews, was released in August 2009. During the list of people who hate the ringtone, once the lyrics get to "all the Pakistanis", Osama bin Laden can be seen hiding behind them. The existence of the Abbottabad compound wouldn't be revealed to the American public until almost two years later.
In the song called "Yoda", we have the line "I'll be playing this part 'till I'm old and gray." Mark Hamill may not be gray, but he certainly is old, and he is still going to be playing Luke in the upcoming sequels.
And, by the way, if one day you happen to wake up and find yourself in an existential quandary, full of loathing and self-doubt, and wracked with the pain and isolation of your pitiful meaningless existence; at least you can take a small bit of comfort in knowing that somewhere out there in this crazy old mixed-up universe of ours, there's still a little place... Called Albuquerque!.
"White and Nerdy" has a line that mentions social networking site MySpace, which was overtaken by Facebook in terms of popularity just a few short years later.
One of the songs from that album, "Stop Forwarding That Crap to Me", had Al ranting about unwanted things being sent to his email address. In the same vein, one of those happened to be unicorns, one of the pony races in FiM.
Also, his "Whatever You Like" music video has a parody of Uncle Ben's Rice with "Win a pony" on the box. It's even funnier after his appearance on the show.
"Hold on a minute, there's still at least one hundred twenty-seven more!"
Part of his song "Foil" is about supernatural things like aliens and the Illuminati. A year after releasing this song, he appears on Gravity Falls, which deals with paranormal subjects.
"Tacky" mentions about live-tweeting a funeral and taking selfies with the deceased. Cue Mortal Kombat X, with one character Cassie Cage having a fatality involving taking a selfie with her dead opponent and uploading the pic on social media (and Sideshow Bob would do the same thing with Bart's corpse in the Treehouse of Horror XXVI segment "Wanted: Dead, then Alive").
The Alapalooza album predates the series Grimm by eighteen years and the character Teresa "Trubel" Rubel by twenty-one, although you might think the character was referenced in the song "Young, Dumb, and Ugly" due to the following lines:
We got two-day stubble. Our name spells "Trouble".
The song "Pretty Fly for a Rabbi," talks about a jewish individual named Bernie who is pretty fly. Come 2016 elections and everyone is talking how fly a jewish person named Bernie is.
Never Live It Down: He became so known for singing about food in his early career (even releasing a compilation album of food songs) that many artists approached for parody automatically assume it's about food (most notably Kurt Cobain of Nirvana, who specifically asked Al to not make "Smells Like Nirvana" be a song about food).
Long before Key & Peele got their own online fame, they had a cameo in the music video for "White and Nerdy."
Al's first music video, "Ricky", has the role of Lucy played and sung by Tress MacNeille at a time when she was just starting her voice acting career. MacNeille would later appear in The Weird Al Show and lent her voice on Al's Running With Scissors album.
TMZ. Like many of his other songs, it's a brilliant (if somewhat awkward, see above) parody with strong attention paid to the original. But when you really listen in on the lyrics, you'll realize that it's actually a serious commentary of our culture and how accepting we are of how shameful the paparazzi has become. It's really a Take That at what our popular culture has become and how little we've learned from the Princess Diana catastrophe. This is reinforced in the music video where the celebrity in question is running in the streets. Humiliated beyond words. Beyond comprehension. THAT alone says something.
The song also contains a secondary Take That at entitled celebrities who think their status means they can escape all consequences for their actions.
Phony Calls (which parodies TLC's Waterfalls). Remember, don't go making them...
Sweet Dreams Fuel: His songs can put one in a good mood really fast, and many fans have written to him about he helped them cope with depression.
Tastes Like Diabetes: "If That Isn't Love". Yes, it's supposed to be a spoof of these types of love songs, but one could argue that he spoofed them a little too well, and that the attempts at "twisted" humor fail to offset the cheesiness of the chorus. Not to mention that it's a style parody of Hanson, who are arguably an example of this trope.
For what it's worth, the chorus implies that the narrator has absolutely no idea what love actually is.
They Wasted a Perfectly Good Plot: Let's be honest, Osama bin Laden's death would have been a better subject for "Party in the CIA", despite the fact that Al no doubt wrote the song before it happened.
Al's friend and college note Specifically, California Polytechnic State University, or "Cal Poly" for short. classmate Joel Miller said in Al's Behind The Music episode that he thinks drugs would make Al turn normal.