All right. I’m caving. I’ll do it. I’ve seen Paul do this one. And then Jess. And then Meghan. I’ve resisted because, despite my diverse taste in music, I’m fairly certain whatever songs happen to come up in this thing will be mocked relentlessly. But in thinking a little more deeply about it, I don’t think I should apologize for the music I like to listen to.

So here’s the deal. I grabbed my 2nd generation iPod Mini and put it on shuffle. Yes, I said 2nd generation. It’s old. The last time I had someone under the age of 30 in my car, they complained that the thing didn’t have a touch screen. Deal with it, I bought it in 2007 with tax return money because I was tired of carrying CDs around in my car. Now I have 900 songs at my fingertips. What a time to be alive!

I got off track. Anyway, I put the little musical doodad on shuffle and let the randomness begin. What will follow are my thoughts on 30 songs…

1. The Sign – Ace of Base
I know that this song was a big hit in the 90s. But, honestly, all I think of when I hear this now is the beginning of Pitch Perfect. You know, where the Bellas’ lead singer pukes all over the first three rows. Gross.

2. I Wanna Grow Old With You – Adam Sandler
This song is kind of disgustingly adorable. It’s from the end of The Wedding Singer. A friend of mine once toyed with the idea of having me play and sing this at his wedding. I’m kind of glad he and his bride went with a different song for me to do. Not that this is a bad song. It just sounds weird singing these lyrics when it’s clearly not intended as a wedding song.

3. In the Year 2525 – Zager & Evans
My parents kept the car radio on the oldies station a lot when I was growing up. So I have an extensive background in the hits of the 50s, 60s, and 70s. This song always fascinated me with its depressing look at what the future could look like. I asked my Dad why I’d never heard of Zager & Evans. That’s when the term “One Hit Wonder” was first explained to me.

4. Falling for the First Time – Barenaked Ladies
I went through a pretty serious Barenaked Ladies phase in college. A band I was in started covering some of their songs. I started buying up their albums. It was a little weird. But this song, in particular, brings back memories of the earliest promos for How I Met Your Mother back before it premiered. This song was featured in some of those commercials for some reason.

5. How Will I Know – Pentatonix
Anything by Pentatonix is amazing.

6. Nobody Knows – Tony Rich Project
Ah, unrequited love in the 90s. I think I remember hearing that this guy recorded himself doing all the parts of the song himself. It’s just one guy. Is that true? I know I’m sitting at a computer and have the Google at my fingertips and could easily research this question. But I don’t want to.

7. Cats in the Cradle – Harry Chapin
It’s possible that a lot of people with daddy issues will tear up when listening to this song. But I had a great relationship with my father. I don’t think it would be heartbreaking for my Dad at all if he thought that I’d grown up to be like him.

8. Miss Independent – Kelly Clarkson
What if I don’t have a particular memory to go along with a song that comes up? This one doesn’t really stir anything up.

9. Angel to You (Devil to Me) – The Click Five
So there’s another song by this band that really reminded me of a relationship I had with a girl I knew during college. Because of that song, I bought this album. And then I did this thing where I listened to this CD in my car on repeat for roughly two months. I had that thing committed to memory.

10. The Show – Lenka
I think Brad Pitt’s daughter sang this in the movie Moneyball. I liked it. So I found the original version and downloaded. It’s catchy.

11. She’s Got a Way – Billy Joel
I feel like this one reminds me of a girl, too. There are just some songs, I guess, that I became obsessed with at the same time I developed a crush on someone and those songs are forever intertwined with memories of those girls. It sounds kind of pathetic. But I really didn’t date much in college. Still don’t. Back then I just sort of liked girls who liked to give me the “we’re just friends” speech. You could put that on repeat on my life’s soundtrack.

12. Midnight Bottle – Colbie Caillat
During my North Carolina years I went through another phase where I wanted to hear everything that Colbie Caillat ever sang.

13. I’ll Stand By You – The Pretenders
I had this one on repeat when a friend of mine was going through a really difficult time and it seemed like everyone close to her was abandoning her.

14. The Wind Beneath My Wings – Bette Midler
When I was a kid, I took piano lessons for about three seconds. In preparing for a recital, my piano teacher somehow found out that I had a decent singing voice and asked me to sing this and she would accompany me. Thankfully, that was before my voice changed and I could comfortably sing in Bette Midler’s range. Who am I kidding? I can still sing comfortably in Bette Midler’s range.

15. Dust in the Wind – Kansas
“You’re my boy, Blue!”

16. Defying Gravity – Idina Menzel
I’ve never seen Wicked. And as much as I love all things Oz, I feel like it’s something I’d really enjoy. Even though I read the book and really did not like that too much. But at some point, I decided I should get the Broadway recording and learn all the songs. This is actually the only one I’m mildly familiar with.

17. The One That Got Away – The Civil Wars
I loved this duo. I won the Barton Hollow CD through a contest that a friend of mine held on her blog and I fell in love with their songs. It still breaks my heart a little to know that they split up not long after their second album was released.

18. All for You – Sister Hazel
This is another one that the band I sang with covered. We never actually performed this one. It was just one that we messed around with a couple times when we were just sitting around pulling out random songs. The kind of thing that we were doing just to see if we could do it. We could. Not sure why we never actually did it in front of people.

19. Always Be My Baby – Mariah Carey
Mariah Carey in the 90s. Life was simpler then, wasn’t it? She hadn’t had a meltdown on TRL. She hadn’t had a meltdown on NYE. Good times.

20. My God – Sister Act
I love this song. I love singing along and trying to do it in the different nuanced voices of each nun that takes a solo line. Especially the nun that shouts, “AND I’M GONNA!” Cracks me up every time.

21. Space Oddity – David Bowie
I’m almost ashamed to admit that my first real exposure to this song (despite listening to the music of the 70s throughout my childhood) was in the movie Mr. Deeds when Adam Sandler started singing it on the helicopter.

22. Saying Goodbye – The Muppets
This one is from The Muppets Take Manhattan. In my opinion, one of the better Muppet movies. Did you see the video I posted where I did the different Muppet voices during The 12 Days of Christmas? I like to sing along with this one with the different voices, too. I have fun trying to do voices. I think I want to be Robin Williams when I grow up.

23. After All – Peter Cetera & Cher
I can’t believe I’m blanking on this. It’s in a movie. It had Robert Downey, Jr. who played a guy who was reincarnated and he could remember his former life where he was married to Cybil Shepard. I wanna say Chances Are… Maybe? I don’t know. Again, I could look it up, but I don’t want to.

24. A Page Is Turned – Bebo Norman
There was the possibility that I was going to sing this in a friend’s wedding at some point during the college years. So I took the time to learn it. And then I never sang in that wedding. Or that wedding never happened. I can’t remember. I may not even be in contact with that friend. Former friend? Minor acquaintance?

25. One Sweet Day – Mariah Carey & Boyz II Men
In high school, we may all believe we’re immortal. But, when we were in high school, and this song was first released, I think a lot of us claimed that, if we ever died, this is what we would want sung at our funerals. If…

26. Rolling in the Deep – Adele
What was the world like before I was introduced to Adele’s voice?

27. Unwell – Matchbox 20
This is another one that I don’t really have a profound connection to or memory to tie in with… I just like it.

28. Kiss from a Rose – Seal
It was the summer of nineteen-ninety-something… I think this was the first time I realized that radio stations play the same five songs 15 times a day for three months. This song was one of them. Thanks a lot, Batman Forever!

29. Absolutely Zero – Jason Mraz
Man, nothing profound with this one either. But I do like pretty much anything that Jason Mraz puts out. I find that our vocal ranges are similar, so it’s fun to sing along with his stuff. Including this one, even though it’s a little slow and kind of dull in my opinion.

30. Runaway – Del Shannon
And we’ll end things with another oldie. Pretty sure this one is from 1963. I don’t know why, but for some reason I remember this song being a favorite of mine when I was a kid. I mean, if you listen to it, it’s kind of depressing. But it’s so upbeat at the same time.

Well that was kind of fun. It’s funny the memories that some songs conjure up. Madonna’s “Like a Prayer” didn’t make the cut this time, but I do feel the need to share that, every time I hear that song, I think of my friend Andy, dressed in a Cleopatra looking wig, making a music video where he dances and perfectly lip-syncs the song. It was flawless.