Let’s be honest, most of us have some pretty horrific iTunes purchases littering our iCloud, or whatever it is Apple wants us to use these days. For plenty of Millenials, our first real music purchase came on Apple’s esteemed music service. (Unless you were hip/old enough to try Napster, in which case… gold stars all around). With 99 Cents of Shame, we look back on some of those mystifying past purchases, attempt to see what appealed to our sixth-grade minds, and find where those wonderful bands are now.

The Context: I became an obsessive hip-hop fan around the time I was 10 years old, and since that was the mid-2000s I instantly gravitated towards the sounds of southern rap, which is where most of my education in the genre came from. In my mind, people like Scarface, UGK and T.I. were real rappers, while people like Asher Roth were supposed to be gimmicks.

Still, when “I Love College” dropped in January 2009 I couldn’t deny the appeal. The “frat rapper” had not become commonplace yet, and the song was just too damn catchy. The hook could be remained a million different ways, and as an awkward white kid it was pretty easy to imagine yourself in Asher’s shoes, even if that was never going to be the case.

Why I Bought It: Like every child that grows up in America that follows pop culture, I had a grandiose vision of what my college experience would be from about the time I turned 13. “I Love College” was a major part of that vision.

In fact, I was so infatuated with Roth’s song from the first time I heard it (probably on MTV, but I can’t quite recall) that I listened to it basically non-stop for two or three days, took a break, and then went right back.

It’s probably in the top 25 of my most listened to songs on my old computer, and I would wager I still know 95 percent of the lyrics.

The Song: “Cause I ain’t goin’ out like a sucker no way.” Come on now, tell me hearing that line, followed by a choice Weezer sample, doesn’t make you at least a little bit nostalgic.

At the same time, I’m not going to pretend “I Love College” is high art, or even quality hip-hop. It’s a song about getting baked, going to frat parties and getting with girls performed by a nerdy white guy in monotone.

Roth has improved tremendously as a rapper in recent years (which we’ll discuss shortly), but when his first song came out he was pretty unpolished. His cadence basically stays the same the whole song and his mic presence definitely leaves something to be desired.

If you ask me, Chris Webby’s version is far superior to the original.

Where They Are Today: For someone who burst on the rap scene by calling himself the Hakeem Olajuwon of beer pong, Roth’s story actually ended quite well.

He never had another single that matched the success of “I Love College,” the closest was 2010’s “G.R.I.N.D.,” but his debut album sold well and Roth remade himself as something of an old school backpack rapper.

He dropped an outstanding EP with producer Nottz Raw called The Rawth, and put out a few solid mixtapes while embracing his innate humor and knack for wordplay.

Roth is probably never going to have another single reach the heights of “I Love College,” but he has carved out a niche for himself in the rap game and could have a long career if he ever finds someone to release his second full-length.