Hip HopLegendsOriginal ArticlesWorldWide NetworkWWETV ExclusivesWWETVN Exclusives

If Hip Hop Had An Old School Draft? My 1st Round Pick!

Who Is Your #1 Draft Pick From The Old School?
  • Add your answer

Vote for a male and a female rapper as your representative for your #1 draft picks. Every Saturday for Old School Saturday on WWETV Network the top male and female will be featured until they get knocked out of their draft spot!!! Let's see who wins most of the weeks!!

This is Venom once again with an exclusive piece. Some people were asking if I was a male or female because of my last article about women empowerment in entertainment. Does it really matter? As long as I bring that heat for you to read that should be the focus.

In June of 2018, someone asked the question if there was an old school draft pick who would you pick? The question was a good one and was also a tough one with so many legendary MC’s who changed the rap game over the years.

Now this photo above is without a doubt a legendary collection of rappers, but does it truly represent the old school when you only see rappers that go back to the 90’s? It is even arguable that some of these rappers shouldn’t be on the list since they came on the scene in the late 90’s or 00’s.

However, then I realized that someone like Eminem, Cam’ron, and Lil Wayne have been on the hip hop map if not 20 years pretty damn close to it. So they would be considered old school to fans of hip hop today.

Let’s go on a little hip hop history however and analyze those listed in the picture. At the bottom right corner we have 50 Cent who is one of the last hip hop artists to go diamond around the time of his releases instead of how it is today where artists take years to accumulate those numbers due to how the streaming era has changed how music is consumed. Still it can’t be denied that Curtis Jackson was HUGE when he came out with Get Rich Or Die Trying. I wouldn’t pick him as my first draft pick though. He could sell and he had a marketable image, but he has limits which I will get into later that a lot of rappers entail which I wouldn’t draft 1st for the very same reason. If the draft was someone who would be the poster boy or girl for this new music called hip hop I would stay away from a very destructive force such as Curtis Jackson who went to beef with everyone and didn’t vary his rap messages to America about the plight of the inner cities. I believe this is very important when choosing the 1st round draft pick for the first hip hop star to represent the genre for mainstream acceptance and appeal.

50 Cent

I also see at the center top of the picture the iconic L Boogie aka Lauryn Hill. There is no doubt she helped to create one of the industry’s greatest albums ever. Hill was a monster MC which some younger fans of hip hop don’t know about because her negatives that lower her all time rank has to do with her not making new music for years. I love Lauryn Hill, but that disqualifies her from being my 1st round draft pick. I need someone who could sustain this new artform and Lauryn Hill is quite unstable in that department with her tardiness and lack of new material. In her prime, she is definitely a candidate with her Afrocentric image representing black women and dual position of singer and rapper that paved the way for the likes of Drake.

Lauryn Hill

Now speaking about female rappers, I do feel this picture is very disrespectful to the women who should be acknowledged as the true old school. Where is Roxanne Shante the actual female that the coin female rapper was made for because men didn’t want to crown her as the King Of Rap?

Where is MC Lyte? Where is Queen Latifah? Where is Monie Love? The hip hop artists from “Ladies First” actually showed the mainstream world of the growing women movement at the time. Even if the person asking the question is more familiar with the 90s where is Lil’ Kim, Foxy Brown, Missy Elliot? 

For many people of the early days of hip hop Sha Rock of Funky Four Plus One would be the first round draft pick of hip hop as she was one of the original ladies to be presented at shows.

Funky Four Plus One

Now that I gave that little history of women originators of the hip hop genre I will start to make my top 5 list and then break it from there to announce my 1st round draft pick. I would definitely consider a woman to be a possible draft pick for many reasons.

I would think it may be possible to market her to a doubtful audience of this new genre. She would be marketable and someone who could visually compete with the likes of other women in the music industry. Since the question is about old school, I am assuming this will be in the era the question is posed with 90’s and 00’s era. That would mean my female pick would need to compete with the stars of the day such as Beyoncé, Aaliyah, Janet Jackson, Rihanna, etc. Lauryn Hill is the easy answer, but I already explained why I would not choose her.

So I’ll pick two women and then pick three men as my top 5 and pick a winner from that bunch. My two leading ladies would be Lil’ Kim and Missy Elliot. The reason being 90’s Lil Kim was a beauty and a monster on the mic. She also captured the eyes of America when she debuted. As she recently stated in an interview it was the streets of New York that proclaimed her the Queen Of New York and she definitely held her own with the King Of New York Biggie Smalls. I can’t see how she couldn’t be a contender for 1st round draft pick. Her downside was her raw lyrics and at times profane content. I would be hesitant thinking the backlash would hurt hip hop’s long term potential.

Lil Kim on Talk Show About Her Explicit Content in 1996

However, with that possible downside I would also know that she would definitely garner me buzz and interest for this new genre. My other draft pick for a woman would be Missy Elliot. She is the exact opposite of Lil Kim in terms of not having extreme explicit lyrics and can be marketed as a non threat to media companies to put on their platform. She is also very creative and would come up with ways to make my new industry work. She actually has more mass appeal for that reason.

Missy Elliot in 1997 talking about her unique style

So now I would be put into the position to choose from the list of so many great rappers it would make my head explode. I’ll analyze those in the picture and explain what I would do in the boardroom if they were presented to me. 

Snoop Dogg

Now Snoop is someone I would consider, but this hypothetical question raises the question of if I knew Snoop would have that issue of his murder case pending. I would definitely want the Snoop of 1993 when he burst onto the scene selling like hotcakes. He also comes with the iconic producer Dr. Dre who changed the rap music production style with his G Funk that had more mass appeal than the boom bap and the previous golden era. My issue picking Snoop is knowing what I know what happens when he drops that first album. He never reaches that level of music greatness again. Don’t get me wrong he still had great hits after 1993, but it is hit and miss. One thing I will give him though he tries to expand his limits by entering into other genres (remember Snoop Lion?), but that only illustrates the frustrations of having him as your #1 draft pick. You need that first superstar to be completely hip hop and who sets the standards for all times.

This is the conundrum I also face if I pick Andre 3000. The man is a lyrical beast, but his creative juices sometimes causes him to not stay true to hip hop either. I would be wondering which Andre would show up when I needed my MVP to deliver.

Outkast Andre

Andre 3000

Now having someone who can be this versatile is always a plus on record label, but this question is about picking hip hop’s #1 draft pick. I’m sorry love these two artists to death, but they seem to do better when they are teamed with certain individuals. Snoop is better with Dr. Dre production and Andre is better imo as Outkast Andre. My draft pick needs to be a solo act who can be diverse with anything thrown at them. To be able to work with any producer I choose for them. This leads me to the rapper who was the first hip hop artist to have a super producer team for his album. The one and only Nasir Jones. 


One of the greatest to ever do it. Nas I would definitely think of banking on to burst this new genre onto the big stage. Born and bred in New York he is hip hop. Lyrically there is none better and he has appeal for the masses with his laid back demeanor. The pressure was on him when he was being touted as the heir apparent to Rakim which is needless to say is something very hard to do. Nas’ negatives is his choice of production for his albums. I would try to pick beats for my new breakout star to push this new genre, but I got a feeling Nas doesn’t take orders on how to create his masterpieces and I can’t blame that at all. He also did have dips where he disappointed hip hop fans, but I can overlook that as my first round draft pick would deliver rap’s greatest album ever in “Illmatic”. 

Another New York entity that came with lyrical assassin was Wu Tang Clan who created a movement that was similar to the origins of hip hop’s crews that permeated the scene in the early 80’s. The three outstanding members from The Wu who are possible #1 draft picks. 

Method Man – Ghostface – Raekwon


Another person, that delivered to all expectations when given pressure was Eminem. As Nas was for New York he was for Detroit. Eminem could sell and he definitely has the lyrical skills to represent as #1 draft pick. His negatives though are his need to make pop songs which is good for commercial success, but I tend to agree with Joe Budden that he does come off as corny at times. I mean who could forget “My bum is on your lips” classic line? I would fear coming out with Eminem first to represent the industry there would be a possibility of the world taking this brand new genre as a novelty act with no long term potential. I would choose someone like Slick Rick over Eminem because he could also deliver songs with storytelling that could be used in various outlets and would display the artform in a manner that is memorable with his laidback non threatening image. Of course we would have the problem of his jail issue for PR reasons which is why he is eliminated as well. 

Slick Rick

Jay Z

The man who is a business….man! You can’t go wrong with having Jay Z as your #1 prospect. He would hustle his way into breaking this new genre due to his DNA that won’t allow him to accept failure. He has lyrics and he has those songs that could get you play on the radio. In recent years, Jay Z has also been able to adapt and vary his content which was always a critique of his. Still I wouldn’t pick Mr. Carter as my # draft pick from the old school batch 00’s back to the 80’s.

Speaking of the 1980’s I do believe the person asking the question has been disrespectful to those who were doing it big in that era. The guys who made people take notice of this new thing called hip hop. Melle Mell needs honorable mention alone just for putting out “The Message” which turned the world upside down and had Grandmaster Flash and The Furious Five touring with the likes of The Jacksons and Rick James. The song also laid the foundation for songs with strong content. Melle Mell also brought the flash and style to hip hop that was comparable to a rock star.  

The problem with Melle Mel is he didn’t seem to know how to adapt when new rappers came onto the scene that changed up the game such as RUN DMC. For this reason I wouldn’t pick him for my first draft pick as I would need someone who can defend his position of being the face of hip hop. This is a reason why I wouldn’t pick MC Shan although he was a huge star that could have mass appeal. He couldn’t hold his position when KRS One took aim at his throne.

The kind of rappers that could fend off any challengers to the throne would be Redman, Kool G Rap, KRS One, LL Cool J, Big Daddy Kane, Chuck D, Rakim, Biggie, Tupac Shakur, and Ice Cube.

Kool G Rap is a legend who doesn’t get a lot of praise from newer fans because he didn’t have the mass appeal which eliminates him as my first draft pick. It is also a reason why I wouldn’t have KRS One or Redman as the #1 pick either. When things got thick against Nelly who he felt was ruining hip hop with making it too commercial he couldn’t overcome it.

Kool G Rap

LL Cool J could definitely defend my new genre if he had the streets coming at him with rap battles, but he could also crossover when needed to do songs for the women. He was also able to be a movie star. He once coined the term GOAT and I think he does get left off many people’s list because they don’t know or forget how hard LL came onto the scene. He was given that decade plus contract by hip hop’s first big label Def Jam for a reason.

Another rapper who turned movie star was Ice Cube who I would definitely consider for my #1 pick as he was able to ignite a whole new genre within the genre with Gangsta rap with The NWA. He also had the tools to be a leading man in movies such as “Boyz In Da Hood” which dictated the temperature of America in Los Angeles at the time.

Although there were other gangsta rappers before such as Ice Cube and Schooly D neither of those rappers were able to create such an American frenzy as Ice Cube could with “Straight Outta Compton” and we saw the impact of the NWA biopic. Cube was a west coast rapper with the skill and training of a east coast rapper which made him very dangerous and versatile. He could also defend himself if any rappers came at him for the #1 spot as evident with the lethal diss song “No Vaseline”.

Ice Cube on New York Old School Classic

DMX is a rapper who would be on my list when trying to make a choice of #1 draft pick. He had crossover appeal and also could reach the ears of the streets with his music. The downfall with DMX is obvious with his demons which include drug use that has been a hamper on his career going further than where it is although he is still in the top ten most selling hip hop artists in history. Just imagine where he would be now if he could handle his vices. It’s for those unstable reasons I would be hesitant to have him as my #1 choice in the draft.


A rapper who had the same kind of militant mind was Chuck D who I would chase to go to war for me and lead the charge. He would definitely stand his ground at any negative feedback the media would throw at him to dissect or try to discredit this new form of music. My only worries with going with Public Enemy as #1 is that same power for the people attitude may prevent the suits who run everything to shut it down especially with today’s political environment with President Trump, MeToo Movement, and politically correct running the system. In the 1980’s, it was a bit different and they also came after the original harmless MCs that broke ground for the genre such as Sugar Hill. Public Enemy didn’t have those party songs for radio consumption that would bring in media outlets that could expand the genre if Chuck D was given the task of launching hip hop.

Burn Hollywood Burn

Another New York rapper took the world by storm and he was also able to jump between hardcore street lyrics and commercial success. You can’t have  a discussion about top prospects to run your new genre without mentioning Christopher Wallace aka Notorious BIG aka Biggie Smalls. We know the legend can put a whole industry on his back and more than deliver as that is exactly what he did for the birthplace of hip hop when it was in a slump against the West Coast rise in the 90’s.

Biggie Smalls

The Notorious B.I.G. is someone who many claim is the GOAT, but even with those accolades I still have two other hip hop artists I would choose for the #1 pick. Keeping with the mid 1990’s of course one can’t bring up the iconic Tupac Shakur who is another artist that gets the “Greatest Of All Time” title to his name by hip hop fans. I will say without a doubt Mr. Shakur had the most influence on rappers who followed him and if we are to believe him in interviews he also influenced Biggie Smalls. 

Tupac also checks off in the crossover section as he made music for women and men. He also had a mass appeal that garnered him leading roles in movies such as “Juice” which lands him in the area of LL Cool J and Ice Cube. Could you depend on Tupac Shakur to defend his #1 position? Without a shadow of a doubt he could hold his own against contenders. The biggest aspect of Shakur that has him leading above everyone else is his aura to make a movement or revolution out of your new genre.  He was well spoken and knew how to handle the media. He was also a star that touched the hearts of the people that still resonates today with the classics of “Dear Mama” and “Brenda’s Got A Baby”.

Tupac Shakur Brenda’s Got A Baby

We know we can depend on Tupac Shakur to lead your revolution, but there is one major flaw that eliminates him from my number draft pick. Tupac’s hotheaded nature was a negative that lead to his death. He has become immortal like no other rapper in history and probably ever be, but I would have Tupac Shakur as my #2 draft pick. It will become apparent and I believe many will agree why I chose my top prospect to lead instead of Tupac Shakur. So if Tupac and Biggie aren’t my #1 draft pick who is?

2Pac & Biggie

Biggie Smalls once stated how powerful Tupac and himself were that they created a whole coastal war. That is very true and is a reason why I would have someone overseeing this all-star squad I would create to launch this new genre of hip hop.

Biggie Talking About Tupac

I stated earlier I would have a top 5 roster that included Lil’ Kim at #5 and at #4 would be Missy Elliot representing for the women. With these men who follow I believe they would have much more impact on the minds of the world to carry this new form of music to unseen heights that Lil’ Kim and Missy Elliot couldn’t. That means with what I just stated above Biggie Smalls would be #3 behind my #2 Tupac Shakur. So who would be my absolute number one draft pick?

Big Daddy Kane vs Rakim

It comes down to a few things that I believe Big Daddy Kane and Rakim possess to be my #1 draft pick. It’s the age old question from the 1980’s which was who is the better MC? Kane or Rakim?

Big Daddy Kane

This answer is not so easy to give, but these two men do make it hard for me to choose. Given the topic at hand I am able to at least break down plausible reasons why I would choose one over the other. That means one of them doesn’t make the top five for the roster, but that is strictly for the very good coaching job I would do in having these men alternate their position when needed coming off the bench to “get the job done” as Big Daddy Kane says in the video below.

As you see Big Daddy Kane definitely could appeal to a woman audience (dating Madonna and as he said above comparing himself to the likes of R & B icon Bobby Brown), but he was not limited to only that demographic as he could rhyme with the best of them. Not too many songs even until 2018 are touching “Aint No Half Steppin”. 

I could trust Big Daddy Kane to also defend himself in rap battles and hold his spot as the #1 draft pick. He is a total package just like Tupac Shakur, Biggie Smalls, LL Cool J, and Ice Cube, but the difference with him is he laid the groundwork for all those mention with his rap style.

He checks off in that one department that none of the other mentioned in this whole article do and that is affecting the future of how the artform is executed. He is the author as he says in the song “Aint No Half Steppin”.  There is only one man who can override Big Daddy Kane in this department and that is the Rakim who many call the “God MC” because how he completely revamped the game with his prophetic claim telling people to “Follow The Leader”.

Rakim is considered to be the father of modern day rap that everyone follows with wordplay and rap schemes. He was also a rap star that represented the birthplace of hip hop. When you have the likes of KRS ONE is a teacher of emceeing he has the respect of the original pioneers. 


Rakim also hit the mainstream although not in the way that guys like 2pac, LL, and Ice Cube he was called upon to be apart of soundtracks such as Juice which had Tupac Shakur.  


This is very important time in history as hip hop stars were crossing over such as Tupac and Fresh Prince Of Bel Air(who I would actually have thoughts on adding to this list for reasons that Ice Cube and LL Cool J are), but this also shows the point where Rakim as your #1 pick becomes questionable in the draft as those right after him in the same era excelled to greater heights bringing new eyeballs to the game. It is a reason why I choose Big Daddy Kane over him along with Kane being more equipped for battling contenders proven by his reign in the Juice Crew against enemies. 

Big Daddy Kane also proved he could handle the squad like a captain(Roxanne Shante tells the story above how Kane kept his composure during the KRS One beef with Juice Crew) which would be needed to help my wildcard player and MVP Tupac Shakur when he got into soldier mode. I always believed his energy needed someone he respected to help navigate him better to lead. Tupac Shakur is known for battling the east coast, but many don’t know that he really did have love for the old school New York scene and was originally named MC New York. He was also a student of the 5 borough rules of hip hop, but he had a vision to take it to another level.


This is why Big Daddy Kane would be my #1 draft pick. He would be the player who could manage the court and had the most potential to cool off any heat on the squad that I put together to showcase this new artform. I can hear doubters right now saying no one could contain the powder keg, but as you hear above he was a fan of the pioneers. He also did a tribute to the east coast.

Old School by 2pac

So you can see why Big Daddy Kane is my choice. He had that elder statesmen aura to him and hit all the check marks, BUT the aspect of knowing how to adapt and advance the culture(by including the west coast) that Tupac Shakur had in terms of vision. However, Tupac’s nature was explosive and needed a captain to contain it and know when and where to unleash it. If Big Daddy Kane couldn’t handle the #1 draft spot I would then pass the ball to Rakim to be my point guard. With that said, I leave you with the listening pleasure of Big Daddy Kane and Tupac Shakur on the “same song” showing that Tupac had no problem hanging with him lyrically. 

Check out WWETV NETWORK streaming of “Old School Saturday” with the icons of music.

Hip Hop’s #1 Draft Pick

Also check out the The Legends section.