Lamont's Lists: The Top 50 Hip Hop Songs Of All Time (30-21)

30. The Choice Is Yours - Black Sheep (1991) - No song in hip hop history generates more unbridled enthusiasm than The Choice Is Yours. It's still impossible for your heart not to skip a beat (in anticipation of jumping up and down like a crazy person) as soon as Dres starts to deliver his tantalizing "Engine, Engine number nine..." build up.

29. Nobody Beats The Biz - Biz Markie (1988) - Only Biz Markie could take a simple jingle from a local record store and turn it into an enduring dance floor staple. It was no doubt propelled along by a dope beat from Marley Marl and an infectious hook from TJ Swan, but Biz's showmanship is what made this one into a beloved hip hop classic.

28. Straight Outta Compton - N.W.A. (1988) - In the summer of '88, NWA lit a fire that has never burned out with Straight Outta Compton. Like a moth to a flame, we were drawn into a scary, violent world of sunny Los Angeles that we never knew existed. 

27. Lost Ones - Lauryn Hill (1998) - If we never hear a new verse from Lauryn again, we'll always have Lost Ones. Her voice, delivery and powerful words here are simply majestic. We are eternally grateful.

26. Incarcerated Scarfaces - Raekwon (1995) - Rae said he wrote Incarcerated Scarfaces in 15 minutes one night while vibing in the studio to a scintillating Rza track that was originally intended for his fellow group member Gza. I'm still awestruck by the idea that a sudden burst of inspiration turned out to be his (and maybe the collective Wu-Tang crew's) best song ever.

25. I Got It Made - Special Ed (1989) - Back in '89 a talented 17 year old street poet from Brooklyn linked up with his cool ass neighbor (the super producer of his day, Hitman Howie Tee), who laced him with a dope beat for his debut album that was built around a glorious Ripple sample. Howie's track was irresistible, but Ed's laconic vocals and laid back charisma demonstrated that he was a "supa dupa star" in his own right.

24. Mama Said Knock You Out - LL Cool J (1990) - It was actually LL's grandma who gave him the line that fueled his early 90s resurgence. But that's beside the point. If I was making a list of the most memorable opening lines in rap history "Don't call it a comeback..." would have to be at or near the top.

23. Mind Playing Tricks On Me - Geto Boys (1991) - Speaking of inspiration from grandmothers, Scarface (who wrote all the verses for Mind Playing Tricks On Me) said that it was his granny who fed him that line after he overheard her talking to herself one evening. A bleak song by a little known crew from Houston - and one of hip hop's first to wrestle with paranoia, depression and PTSD - it was just too damn catchy to be denied.

22. Raw - Big Daddy Kane (1988) - Many old school hip hop heads consider 1988 to be the creative peak for the art form, given the incredible volume of great music that was released that year. Dropped that summer, Raw, featuring Big Daddy Kane's composed-yet rapid-fire, smooth-yet rugged and complex-but easy-on-the-ears lyricism, is typically offered up as Exhibit A in any "best year ever" argument. Some 35 years later, it still makes a pretty compelling case.

21. The Show/La-Di-Da-Di - Dougie Fresh & The Get Fresh Crew (1986) - I know I'm cheating here, because these are technically 2 songs. But I mean, come on...has anybody ever listened to one without immediately playing the other? I could write a whole post about how much I love The Show and it's underestimated B-Side, La-Di-Da-Di (which went on to become one of the most sampled songs in history), but suffice it to say that to me they represent hip hop at its most joyful. 

Check Back Later To Find Out Which Song Is #1