By Chad
Hey Readers! Another Nostalgia Oasis article coming at ya!
As I write this, Ken and I are coming off a pretty cool Weird Al Parody Songs podcast series we did that began all the way back in November of 2025. If you aren’t in the know about this, go back into our podcast archives and look for Episode 29, Episode 37, Episode 43, and Episode 48, and a mini episode, Episode 48.5, which takes the four winners of each bracket where they pit off against each other for ultimate Weird Al supremacy!
For our podcast, we have a Google Spreadsheet that we started when we first launched the podcast, and over the years we’ve been in the pod business together, we’ve used this spreadsheet to organize our recording and drop days, throw in ideas to what we call our “topic tank”, and other things that help us with our consistency and improve our quality of what we like to put out there. The idea for the Weird Al tournament was 100% Ken’s idea. Before last year, I would call myself someone who knew what Weird Al’s schtick was, knew a few of his popular parodies, but in no way would I have called myself a fan. He was someone I figured had to be talented to have the longevity in the music industry for well over 40 years, but as the tournament went along, I grew to understand and take an even deeper dive into his discography and style of writing, and with that came a new respect for his talent and contributions to music and pop culture. I would say the personal highlight for me came back in June when, on a whim, I decided to buy a ticket to his show. I figured the concert wouldn’t be sold out, and sure enough, a few hours before the event, I loaded up my Ticketmaster app and headed to the show. Just me, no one else. I am not historically a big concert goer, and certainly not one to go alone, but I don’t know anyone else living here in my area that I have even discussed Weird Al with, so I didn’t think anyone I knew would be interested.
Weird Al embarked on his concert tour, called the 2026 Bigger and Weirder Tour, earlier this year, and his stop in Charleston, which was probably pretty rare for him, was a pretty fun show. His show opened with an act by Puddles Pity Party, which I admit was a pretty strange bit, and I knew nothing of what the sad silent clown was all about prior to the concert, but it seems like the type of act that relates pretty well to a Weird Al comedy show. After Puddles finished about 20 minutes later, on the video screen, the scene cuts to Al walking through the corridors of the North Charleston Coliseum – doing things and bits that were right in his wheelhouse, and the whole thing reminded me a bit of what Morgan Wallen does at his concerts – except Al didn’t walk out with anyone but himself. And what ensured for 2 more hours was Al doing most of his hit songs. From the 1980s all the way to the 2010s. All the popular ones, and Al even took breaks between the songs which I soon realized was a way to change into the appropriate costume for the next song. During the wait, the video board would show clips of Al in pop culture, from his animated appearance on the Simpsons, to clips of him on Talk Shows and other television interviews. It certainly showed that Weird Al was someone who engrained himself into pop culture by sheer wit, irony, fantastic timing, and most importantly, brilliant songwriting skills. His music and song subject matter are a good look at what the last 40 years has been like living in our society.
In my opinion, Weird Al’s career is a tale of two halves. His beginnings in the early 1980’s showcase some of music’s top songs from legendary artists. Michael Jackson, Madonna, Cyndi Lauper, Queen, Survivor, James Brown. As the 80’s gave way to the 90’s, the music scene changed and Weird Al took on a new set of styles, genres, and artists. Nirvana, Red Hot Chili Peppers, Coolio, MC Hammer, Billy Ray Cyrus and then later into the 90s with artists and bands such as the Backstreet Boys, TLC, The Offspring, and even as we entered a new millennium, artists like Eminem, Nelly, Avril Lavigne, and Green Day had songs parodied by Al.
Al’s career, much like other musicians, has been greatly assisted by the advent of a few things that occurred. First off, the launch of the MTV era of the 1980s really assisted Al in being discovered, especially with him also doing music videos to accompany his great parody songs. This would of course be true also in the 90s as he continued to produce comedic music videos that people would remember and Al would never be shy to dress and imitate the musicians he was imitating, or the people he was singing about. Not in a “make fun of them” kind of way. But in a way that the artists he would parody could do nothing but tip their hat at Yankovic’s comedic chops. To a musician, when Weird Al came-a-calling for your song, it was almost like it was Al giving you some kind of musical achievement award that signified “You’ve Made It – I want to parody your song”.
Along the way, there were other ventures he tried. Al-TV was his sort of creative sketch comedy outlet that would air on MTV and VH1 sporadically for many years. Al would inject himself into previously recorded interviews of musicians and celebrities. His 1989 low budget film “UHF” was not any sort of commercial success, but has grown into a cult classic among fans today.
As the internet came along in the early to mid 2000’s, and the start of things such as YouTube, MySpace, Internet Memes and Viral Videos, this did two things for Weird Al. First, as it relates to YouTube, it gave Al a way to continue to produce music videos, as this was around the time MTV was shifting their focus from music television to more reality-based shows and programming. Secondly, the takeover of the World Wide Web gave Al even more content and subject matter to discuss in the years to come. His later work would focus more on internet culture – memes, viral moments, social media, and other concepts that were not even on the radar in the 80s and 90s.
Al always has his finger on the pulse of American society. What we (as a society) think is funny, cute, or cool at a given time is always something Al is monitoring. And history shows us these things are front and center for a short time – the 15 minutes of fame rule – and then fizzle out.
As Al is finishing up his 2026 Bigger & Weirder tour later this month, and his 67th birthday approaches, you have to wonder how long Weird Al is going to continue to tour, write and produce songs. He’s already given us 2 or 3 lifetimes worth of content, so it’s not a question of has he done enough. He certainly has. But as we get closer to another decade, it’s been over 10 years since Al has done a studio album (2014’s Mandatory Fun) – you gotta think for that amount of time, a new set of events, styles, trends, fads, musicians, and musical acts have come about that could give Al more meat on the bone for one more album. Maybe a farewell album, maybe a love letter to the music industry. Either way, he’s done enough to choose how and what (if anything) he wants to do as he approaches his 70s.
I thought as I continue to discuss the podcast, Weird Al, and everything I’ve learned about his career, it would be fun idea to give Al some homegrown ideas right from my brain, and then, take those ideas and put them into AI (not AL) and see what a system like ChatGPT could do with a little bit of information input to see what it can spit back out. Here you go Al, not that you certainly need it, but here’s some inspiration if you were ever out of ideas in that head of yours.
The List
- Post Malone – you gotta think this is a perfect artist for Weird Al to take on. Pulling off the look alone would be worth the price of admission, but also parodying some of Post’s top charting songs like Congratulations from 2016, 2017’s Rockstar, 2019’s Circles, or even 2024’s I Had Some Help (feat Morgan Wallen) would be considerations.
Moneymaking AI Idea – Virals (parody of “Circles”) – Weird Al sings about people and events that went Viral, and the obsession society has as a whole to be famous, or discovered, or “Go Viral”. Of course Al would be tatted and pierced and even have the grill to mimic Post Malone. This could feature cameos from personalities and events you may or may not love like “Hawk Tuah”, Baby Shark, did you hear Yanny or Laurel, Tiger King, the Will Smith/Chris Rock incident of 2022, the infamous cheating couple at the Coldplay concert, Raygun’s Break Dancing in the 2024 Summer Olympics, the craze of Stanley Tumblers, Kendrick Lamar and Drake’s beef, and so much more! - Taylor Swift – this wouldn’t be a first for Al, as he parodied Swift back in 2011 in his song TMZ, but since then, Swift has grown into one of music’s most popular and highest grossing musicians in history. As she has grown up (and gotten married), you’d think it would be appropriate to come back to the Taylor Swift catalog and put his trademark stamp of approval on her career yet again. An appearance by Al dressed up as Chiefs Tight End Travis Kelce seems fitting.
Moneymaking AI Idea – Fortnite (parody of “Fortnight”) -this may not be one of Taylor’s most known songs, but in my opinion it wouldn’t matter. The title alone would suit Yankovic perfectly to discuss the phenomenon of the popular video game released in 2017. Other video games could be included here as well such as Minecraft, Roblox, Pokemon Go, and even social media crazes like Candy Crush, Wordle, and even as far back as Farmville, Words with Friends, etc. - Shaboozey – his debut hit “A Bar Song (Tipsy)” was such a popular song a few years back, that you would think this would still resonate with music lovers.
Moneymaking AI Idea – A Car Song (parody of “A Bar Song”) – this could be Al’s ticket to discuss the popularity of ridesharing apps (Uber, Lyft) as well as the rise of food delivery apps (Doordash, Uber Eats) and our society’s reliance on convenience when it comes to online ordering, Amazon, etc. Things being brought to us rather than going out to get it ourselves. There could even be room to sing about other future Apps and concepts and the conveniences it provides (drone deliveries). And what song that parodies the car experience of current times would be complete without a reference to Tesla and self-driving cars, Elon Musk, and even the Cybertruck! - Sabrina Carpenter – someone who seemed to me to come on the scene out of nowhere, but her presence and popularity in music can’t be denied. It might be a bit early for Weird Al to bestow on her a parody song (remember – Al’s “Seal of Approval” should mean something to most musicians), but ChatGPT had a pretty good idea when I tossed the concept over.
Moneymaking AI Idea – Costco (parody of “Expresso”) – this could be another Weird Al trope of something common in everyday life that he magnifies times 100. One possible bit could be something that starts innocently: “I just need toilet paper.” Then three hours later you’re pushing a flatbed cart containing 48 batteries, a kayak, six pounds of cheese, a patio set, vitamins, a rotisserie chicken and enough paper towels to survive civilization’s collapse. Don’t forget the song must include a part about sampling food inside of Costco all day, and perhaps ending the trip to the store with the famous $1.50 Hot Dog and Drink Combo which I’m sure Al would give that staple of Costco its just due. - COVID and the Worldwide Pandemic of 2020 and the years that followed – not sure what artist or song this would parody, but it seems almost a given that if Al were to produce another album, a song related to COVID-19 would have to be somewhere on the track list. Not sure who, or what, but the amount of material that song can have would be plentiful. Masks, Social Distancing, Vaccines, Quarantine, COVID Tests, and even a part about the President suggesting people take a disinfectant to prevent the spread would all be fair game.
Moneymaking AI Idea – Sanitizing Wipes (parody of “Blinding Lights”) – once again, ChatGPT came through in the clutch. It had a few other ideas, but this one I thought was the best. And it gives Canadian musician The Weeknd, who has already gotten one tremendous honor and been a part of the Super Bowl Halftime Show, yet another notch on his belt. - Old Town Road – it seems like this song, from Lil Nas X with Billy Ray Cyrus making a brief comeback, is a sitting duck just screaming for Weird Al to take this 2019 hit and run with it. Now we need a subject matter that all of us can relate to – what can ChatGPT come up with?
Moneymaking AI Idea – Old Password (parody of Old Town Road) – and there it is. ChatGPT for the win! I even thought of a possible line for the chorus – “I Keep Tryna Log In with My Old Password!” and then the song goes on to discuss the daily challenges and frustrations with trying to login to websites, minimum password lengths, needing security codes via text, facial recognition, 2 Factor Authentication, CAPTCHA systems that are hard to read or decipher. I’m sure Al would have just enough there to fill out the Old Town Road song and make it a hit!
Well, that’s all the time I have for now. Six AI-Assisted ideas for Weird Al to use (free of charge) in case he gets bored and wants to produce another album.
I appreciate you reading this part tribute, part “tongue-in-cheek” article. Overall, I mainly wanted to jot down my thoughts on the music and comedy icon and living legend himself. Nothing here is too serious of course, and that just seems fitting for an article about this musical genius!
Ken