Here we go …

65. The Senior Pep Rally that I may have mentioned before – a large group of us tried to learn the dance from the Will Smith video. We dressed in white button down shirts and black ties with sunglasses and the whole shebang. I remember rehearsing whenever we could squeeze in a few moments. I also remember flailing about and failing miserably. I am not only tone deaf, but I have no rhythm. I am the least musically inclined individual in the world. But hey, humiliating yourself in front of the entire student body for the good of the collective should be on everyone’s bucket list.

Will Smith, Men In Black (1997)

66. Sticking with the Will Smith train, this song takes me to our annual Spring Fling (a day of school spent in the great outdoors wherein 7^th -12^th grade classes competed against one another in a myriad of various silly and athletic contests. So basically a required day of attendance, but spent with friends goofing around on school grounds while tanning ourselves- and maybe winning at something). This Spring Fling was circa 1998. A small few represented our senior class in the good old Lip Sync Competition. I can’t remember if we won.

Will Smith, Miami (1997)

67. This makes me crack up every time I hear this song and it’s totally not a funny song. AT. ALL. It’s one of my favorite songs from back in the day, but it’s the context in which it was used that makes me laugh. Our video team, bless their hearts, used it as part of the soundtrack to our senior video (a VHS montage of various classmates grinning and doing stupid stuff to the melodramatic musical stylings of the 1990s). The reason this one cracks me up is because though on a shallow level listen, one might think the song is about reminiscing Freshman year and how fast times flies, etc. (which is likely why it was used in the video), but on closer inspection it’s actually about a dude remembering his girlfriend’s suicide with an implied abortion entered into the mix. Like I said – NOT. FUNNY. AT. ALL. Probably shouldn’t have been the background music to moments of mad antics, but alas, it is what it is and that is where this song takes me.

The Verve Pipe, The Freshmen (1996)

68. I love Green Day. I loved Green Day back when they were brand spanking new. I particularly love this song. It was sung by our senior choir at graduation and whenever it plays, I think about being on those risers in the gymnasium with my fellow classmates singing it to our friends and families all over again.

Green Day, Good Riddance (1997)

69. This song sums up the area in which I grew up. We kept religion in our little Podunk public school long past the point of political correctness. I’m pretty proud of that. It was sung by my classmates and me at the end of our graduation ceremony. It was actually a rather contrived cheesy moment, but it was put forth would good intentions, and again, defied the laws of the land in a public school setting.

Michael W. Smith, Friends (1987)