December 5, 2020

The Worst ’90s Graduation Songs in Honor of the Worst Year Ever

TGS contributors Tim Johnson and Sylvia June are two old coots who were lucky enough to graduate two decades ago in the 90s, when the world was riding high and Donald Trump was still a shady businessman who hadn’t yet gleefully yelled “You’re Fired” on national television.

Instead of trying to pick uplifting graduation songs for the unlucky class of 2020, Tim and Sylvia decided to let this year have what it really deserves — the worst graduation playlist of all time. Read on as they lay out their picks. Whose list will be crowned Grand Champion of the Trash Heap? Only you can decide!

Sylvia June10:34 PM
Where you at, Mr. Bat?

Tim10:37 PM
Alright, let’s do this. How do you wanna kick this off? Maybe with a little introduction to our readers?

Sylvia June10:39 PM
You decided you wanted to challenge someone to a contest to see who could make the worst mixtape? Why on earth would you want to do this?

Tim10:41 PM
If there is one thing I consider myself to be a connoisseur of, it is bad music. I’m the jerk who spends $5 on the jukebox to make the bar listen to Vanilla Ice for 20 minutes straight.

Sylvia June10:43 PM
OMG NO. I’ve pitted myself against a master. So our category tonight is Graduation Songs, and Tim, you picked the 90s. These are all songs from the 90s. Why this era?

Tim10:47 PM
Yes, as someone who graduated in the 90’s, I heard a lot of gorgeously ridiculous graduation songs. So, this whole thing is kind of equal parts amusement and nostalgia. And, honestly, while the decade is commonly defined by grunge, so many other terrible genres littered the airwaves.

Sylvia June10:48 PM
This is true. I graduated in 2001, which is basically 90s Lite. This makes me wonder, what was your graduation song, Tim?

Tim10:50 PM
My high school graduation was a mess. The class president wasn’t even allowed to take part in commencement. I think we chose What A Long Strange Trip It’s Been by The Grateful Dead. What was yours? Please tell me it was Eve 6’s Here’s To The Night.

Sylvia June10:53 PM
Haha, no. It was Good Riddance (Time of Your Life) by Green Day. Which might be the same thing…but I actually love them both.

Tim10:53 PM
Yeah, that checks out. I actually wondered if that would’ve made your list.

Sylvia June10:54 PM
It’s not on my list for worst! I’ve got some real doozies. Which reminds me, how are we gonna go about drafting our 5 worst graduation songs playlists? Are we gonna flip a coin to see who gets to pick first? We don’t want to duplicate ourselves, see.

Tim10:55 PM
I figured since this whole debacle was my idea I’d let you choose whether you want to go first or defer.

Sylvia June10:56 PM
Obvs I want to go first, lol. I can’t let you have the best worst song.

Tim10:56 PM
You never know, I might drop a bomb at the end.

Sylvia June10:57 PM
:grimacing: OK, so I’ma start off with “I Believe I Can Fly” by R. Kelly. It’s a terribly cheesy song anyway, and I feel like everyone could tell he was a child rapist. I guess this was still before he was “Trapped in a Closet” though.

Tim11:01 PM
Hahaha! Well, guns ablazin’ on the first song. Well done. I actually only recently learned it was a common graduation song. I just thought it was a song from the soundtrack of Space Jam (a movie much loved/maligned on TGS).

Sylvia June11:02 PM
I mean, I understand that it seems topical and all, but…there are way better cheesy songs to pick that I would have been proud to have as my graduation song. So it’s your turn to draft your first pick.

Tim11:07 PM
Alright, well with my first selection, I’m gonna go with 1999’s “Graduation (Friends Forever)” by Vitamin C. Maybe a bit on the nose, but this song typifies the end of that decade; a sample of Pachelbel’s Canon in D, a high school choir and an awful video featuring an “edgy” Vitamin C, what with her midriff shirt and her dyed hair singing in a high school hallway next to lockers like a bad Jason Biggs movie.

Sylvia June11:08 PM
Ahhh I knew that was gonna be one of the first ones to go. I really dislike when a song tries too hard. That is gonna be tough to beat.

Tim11:11 PM
Yeah, it was basically like a record exec said, “Hey, you know what kid’s like? Graduation. Write a song about that!”

Sylvia June11:13 PM
There is no other reason on earth for that song to exist. OK, so my second round pick is “When I Grow Up” by Garbage. Making mental instability seem cool enough to celebrate is not exactly what graduates should be going for. I mean, having it is just a given, but let’s also remember the song references “golden showers.”

Tim11:15 PM
Oh, I’m a fan of Shirley Manson. Is it okay if I actually like that song?

Sylvia June11:16 PM
Yes! I love the song. But as graduation material, it seems a little dicey.

Tim11:17 PM
Oh, for sure.

Sylvia June11:18 PM
What are you gonna bring to the table next?

Tim11:23 PM
Okay, for my next pick, I’m going with “Graduate” by Third Eye Blind. Not only was this song featured in the seminal movie Can’t Hardly Wait, which revolves around a high school graduation party, but it is performed by just an awful post-grunge poppy “alternative” band who wrote songs about meth and suicide that sounded upbeat.

Sylvia June11:26 PM
Oh nooooooo! I love that song. And Ted loves Third Eye Blind. Let’s just hope he doesn’t read this. Bahaha

Tim11:26 PM
Ted only pretends to read our content.

Sylvia June11:27 PM
I guess we’ll find out. LOL OK, so now we each have two songs. Time for my third pick…hmmmm….I’m gonna follow that up with Semisonic’s “Closing Time.” Who thought a song about getting drunk at bar at a bar and trying to bring home someone to bang would be appropriate for graduation?…wait.

Tim11:30 PM
That one was on my alternate list. It’s a local band so I have a soft spot for them. But, man, didn’t we all find the line “every new beginning comes from some other beginning’s end” to be profound in 1998?

Sylvia June11:32 PM
Yes, yes we did. I love this song, too. It has a soft spot in my heart. Not as a graduation song, though. What’s your third round pick, my friend?

Tim11:37 PM
I’m gonna go with Sarah McLachlan’s 1995 tear jerker “I Will Remember You.” Fun fact: not only is this the song Andy Bernard used to say goodbye on The Office, the late, great Kenny Rogers actually recorded a cover of this. It’s a great song, but it has just become so cliché for any type of reminiscent occasion that it has become too saccharine to feel meaningful anymore.

Sylvia June11:38 PM
Sadly, I think you are correct. Was this the song they had on all those ASPCA commercials with the abused dogs and cats? I bawled every time they came on.

Tim11:39 PM
No, that was “In The Arms of an Angel.” But same kind of sentiment.

Sylvia June11:40 PM
Why am I surprised you remember that? LOL

Tim11:40 PM
I can’t hear any Sarah McLachlan song without thinking of sad puppies. Imagine that as your legacy.

Sylvia June11:42 PM
I mean, my legacy is probably questionable decisions and calling people kitty, so…

Tim11:42 PM
Hahahahahahaha!

Sylvia June11:42 PM
Oh, what will my fourth round draft be? I’m going out on a limb here and saying “The Freshmen” by The Verve Pipe. Hear me out on this. Not only is it hella depressing, it’s…hella depressing. Is this really a graduation song, you may ask? Maybe. Maybe not. But I know for a fact it would be terrible.

Tim11:48 PM
It’s about abortion and suicide!

Sylvia June11:48 PM
I thought it was just about suicide. Are you thinking of Brick by Ben Folds? Because that, I couldn’t imagine.

Tim11:49 PM
She committed suicide because of the shame of having an abortion. It is a dark, dark song.

Sylvia June11:49 PM
Oh noooooo. Well, let’s not play it at our graduation then, shall we?

Tim11:50 PM
Which makes it all the more messed up my girlfriend at the time decided that it was “our song” and I stayed up all night figuring out how to play it on guitar. Well… on that note…

Sylvia June11:51 PM
Yes, what do you have up your sleeve in the fourth round?

Tim11:52 PM
Yeah, moving on. With the fourth pick in the 2020 Bad Graduation Song Draft, the Tim Johnson’s select “My Heart Will Go On” by Céline Dion. Maybe if Rose would’ve moved over like 8 inches, Jack would’ve been able to climb on that door and he would’ve survived long enough to wax nostalgic about the past.

Sylvia June11:57 PM
Oh fuck me, that’s the best one yet. I don’t know any teenage girl in the 90s who didn’t watch Titanic like a dozen times. In the theater.

Tim12:00 AM
And the whole conceit of the song is that it is someone looking at the past and knowing those moments will live on forever. Classic graduation melodrama.

Sylvia June12:01 AM
You’re too good.

Tim12:02 AM
Well, you have one more opportunity to top it.

Sylvia June12:10 AM
I don’t think this pick will, but we’re gonna have to let our faithful followers decide. My final pick is “Shiny Happy People” by REM. I love that it’s so happy, but it feels like an acid trip. Maybe that was the point. I’m not sure. It just feels too positive, which I do concede may have been fine for the 90s. I miss that decade.

Tim12:11 AM
Aww, now I’m getting nostalgic. I’m definitely seeding my next playlist with REM.

Sylvia June12:13 AM
They have some good shit.

Tim12:13 AM
I like that you ended on a positive note.

Sylvia June12:13 AM
Yes, not trying to totally tank the whole list. LOL

Tim12:17 AM
Well, before I get to my last pick, I think I have to get a little introspective. I don’t want to end this without thinking about how far we’ve come. Class of 2020, today is an exciting milestone. I look out at a sea of shining faces and I see potential. I see the future. Still, I must admit some trepidation. How do I say goodbye to what we had? The good times that made us laugh outweigh the bad. (edited) With my final selection, I choose “It’s So Hard to Say Goodbye to Yesterday” by Boyz II Men.

Sylvia June12:25 AM
One of the cheesiest of all time, my friend. Well played. I have to say I enjoy their harmonies, though.

Tim12:27 AM
Thank you.

Sylvia June12:29 AM
I wish I had a meaningful message to give to this year’s graduates. But I don’t. I feel like this year deserves the absolute worst graduation songs of all time.

Tim12:30 AM
I’ll be curious to see what our readers think. We took two different strategies. Your list is definitely full of fun songs on the surface that are really kinda terrible. Ha! I remember in 2019 when I said 2020 was gonna be my year… that aged well.

Sylvia June12:31 AM

Tim12:31 AM
And with that, I think we say, “thank you, dear readers.”

Sylvia June12:33 AM
“Thank you, dear readers.”

Sylvia June | The Tailgate Society

It’s up to you — whose side are you on for the absolute worst ’90s graduation songs? Sylvia’s Side A, or Tim’s Side B?

Side A

  • “I Believe I Can Fly,” R. Kelly
  • “When I Grow Up,” Garbage
  • “Closing Time,” Semisonic
  • “The Freshmen,” The Verve Pipe
  • “Shiny Happy People,” R.E.M.

Side B

  • “Graduation (Friends Forever,” Vitamin C
  • “Graduate,” Third Eye Blind
  • “I Will Remember You,” Sarah McLachlan
  • “My Heart Will Go On,” Celine Dion
  • “It’s So Hard to Say Goodbye to Yesterday,” Boyz II Men
Chaplin
Sylvia June
Sylvia June 27 Articles
Staff Writer

I'm Vee. I live in a cute little house with my cats. I grew up in Northwest Iowa and graduated from Iowa State (where, btw, I first met the notorious Ted Flint over a game of flip cup). Other totally random facts about me: I like goats and I am turned on when people make literary references in everyday conversation.

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