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Author's Preface: I know my homey G. Mittens will be ready to have my neck hanging from a noose for this, but it has to be said.
I go back to the Video Music Box/Yo! MTV Raps days, so this has nothing to do with me not respecting history. “T.R.O.Y” was one of the best songs from the early 90s, but there's an unwritten oath stating this is the one song that will represent what "real hip-hop" was until the end of time. Saying “T.R.O.Y” is the greatest of all time hearkens back to the corny "when did you fall in love with hip-hop?" question from Brown Sugar (Note: I wrote that sentence weeks ago, since which point a female friend playing this song actually said "This reminds me of when I first fell in love with Hip-Hop") I'm sure that true disco heads don't consider "Stayin' Alive" to be that genre's greatest song.
Don't get me wrong, it's classic and it was great for its time just like "I Used To Love H.E.R" was great for its time, but I have no desire to hear either of those songs possibly ever again in life.”T.R.O.Y” is to Hip-Hop what Frankie Beverly featuring Maze's "Before I Let Go" is to classic soul. Say there was a Family Feud segment where they asked a white clan “Name the top 5 foods black people eat” what's the first answer they would give? Fried chicken of course, and while that may or may not be right (barbecue chicken, mac n cheese, candied yams, collard greens, hello?) it's a little off-putting for that to be THE food associated with my people. That's how I see ”T.R.O.Y” as a die hard Hip-Hop enthusiast, the casual listener who goes to a party here and there might say it’s the greatest but that just doesn’t sit right with me.
Pros: an unforgettable horn loop that starts the song and comes in during the hook, it's the commemoration of a departed loved one, etc. It’s like what The Cosby Show was to (black) sitcoms, a feel good family experience aside from the old head laughing all night about the hookers at the party.
Cons: There are no real epic moments as far as the MC'ing is concerned. People are moreso programmed to love the song than anything else, it's been played out and spun to the point where it's really not that exciting despite the massive "OOOHHHHHHHHHH" that erupts the 1,362 nd time you hear a DJ drop it at a party. 70% of people don’t even know the story behind Trouble T-Roy, they just know that when they hear the infamous Tom Scott sample they absolutely must lose their minds.
5 songs off the top of my head that I feel are greater
The Bridge Is Over - http://www.sendspace.com/file/ifvjg5
The Show - http://www.sendspace.com/file/qptawz
Scenario Remix - http://www.sendspace.com/file/a6z2xf
Buddy Remix - http://www.sendspace.com/file/17wac5
HipHop Junkies http://www.sendspace.com/file/vf5xw1