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Orlando & The Freakshow

5 Songs That Didn’t Age Well

By Richie Ortiz

One of my favorite things to do when I have some downtime is listen to my music on shuffle. It always takes me down a crazy path of music I forgot about. As I was getting lost in the shuffle session, I came across a song that made me cringe a bit. Michael Jackson’s “PYT”. I couldn’t help but think about all the allegations against Mike and how the song didn’t age well over time. It also inspired me to create a new list! So let’s have a toast to the songs that couldn’t outrun Father Time. Here are my top 5 songs that didn’t age well.

Why Songs Don’t Age Well

There are many reasons why songs don’t stand the test of time. And one very easy reason is simply being outdated. For example, let’s use technology. There’s nothing that outdates a song more than mentioning a technology that is currently obsolete.

Another reason a song can age is legal troubles. In the beginning, I talked about one of Michael Jackson’s songs and his allegations. It can make a classic like “PYT” seem like an admission of guilt with its lyrics. Makes you wonder whether or not they were trying to secretly tell us something.

Let us not forget about relationships. There’s nothing like a song being written about people who aren’t friends or together anymore. Turns the song from a dedication into a bad memory.

Last, but not least we have the lyrics themselves. Throughout the history of music, there have been so many songs that have lyrics that may have been appropriate at one point but have changed to being not so politically correct. So now that you understand some of the reasons why song don’t age well, let’s get into the list!

  • BIG - Juicy

    The song may be a classic, but the lyrics make part of this song obsolete. “Super Nintendo, Sega Genesis/ When I was dead broke man I couldn’t picture this.” Yeah, maybe back in 1994. Now, those two consoles can be bought for a reasonable price or put on a thumb drive.

  • Lil Wayne - Stuntin Like My Daddy

    Once a dedication to his “father” Birdman, now a memory of the drama Lil Wayne was involved with. You may remember the music video, but this song reminds me of the video of Birdman throwing drinks at Weezy at a concert. They may have reconciled since then, but this song is a constant reminder of the relationship they once had. Do you think they’re still kissing each other in the mouth?

  • G-Eazy & Halsey - Him & I

    This was supposed to be a cute duet done by one of the “it” couples of 2017 but we can’t help but think of that one live performance. No, we aren’t talking about the one where they looked madly in love during Dick Clark’s Rockin’ NYE. We are talking about that awkward one on Good Morning America when Halsey found out G-Eazy was cheating. Ouch!

  • YMW Melly - Murder On My Mind

    We all thought this was a concept song where YMW Melly was talking about a hypothetical murder. Later we found out that this murder might have happened. It was even used as evidence in the murder case he was allegedly involved in.

  • Taylor Swift - Picture To Burn

    I’m sorry Swifties, but not even Taylor Swift can outrun my list. 14 years ago Taylor used the lyric “So go and tell your friends that I’m obsessive and crazy, that’s fine I’ll tell mine that you’re gay!”. Slow down there Swift. It’s 2024 and we don’t say things like that anymore. Since then they have changed them so she says, “That’s fine, you won’t mind if I say”.

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