Pick The Best Rap Songs And We'll Guess Your Favorite Rapper

Music has such an amazing way of bringing people together for a common purpose, and the music played on the radio has a way of telling the story of a generation. We have seen music evolve in so many incredible ways over the years, and we have reached a point in time when music is able to reach more people than ever before. Artists are coming from out of nowhere to rise to the top, and it just so happens that the rap genre is leading the charge into the future.

We are seeing rap take over and dominate the charts like never before, and the genre is heading into new territories, meaning that we the fans have so many amazing things to look forward to in the coming years. Even though rap is much younger than some of the other genres in the world today, what it has been able to accomplish is nothing short of incredible, and the people responsible for taking the genre to where it is now have gone down as legends of the music business.

Today, we are bringing some of the most popular songs in the history of rap to the forefront, and we are giving people the opportunity to either pick or pass each song, compiling the perfect playlist in the process!

Question 1

Pick or Pass “Tell Me When to Go”

Coming from the Bay Area and bringing a sound invoking the Hyphy Movement that swept the youth, this track was nothing short of a local phenomenon when it was released, and thankfully, mainstream audiences gave it their nod of approval. The song flexed all that was great in the Bay, and it helped this legendary rapper catch on with a new generation of fans. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 2

Pick Or Pass “A Milli”

Lil Wayne has been at the top of things for a substantial amount of time, and while he has produced a number of hits during his run in the music industry, this song still remains one of his most popular. It was featured on an album that went on to take the world by storm, and many people were ready to anoint him the best rapper in the world. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 3

Pick Or Pass “Juicy”

Most fans of rap know all of the words to this classic before they even learn the words to what is being played on the radio, and this is because this track was instrumental in reshaping the genre and taking it into uncharted territories. The man behind this track is considered a pioneer of the genre, and this is one of his finest works. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 4

Pick Or Pass “Hate Me Now”

Nas, despite everything that he has been able to achieve during his time in the business, is still one of the best and most underrated performers around. His ability to tell stories and captivate audiences with lyrics is something that truly helped him stand out from the pack, and his willingness to embrace polarizing art also did wonders for his clout. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 5

Pick Or Pass “I Mean It”

There aren’t too many performers from the Bay Area that are able to make it into the mainstream, but this gentleman from Oakland burst onto the scene and has done an exceptional job in remaining relevant by making music that has found a large audience. While the Bay is known for pushing musical boundaries, this performer has been able to lock down crossover appeal. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 6

Pick Or Pass "99 Problems”

This man doesn’t need to make another song for the rest of his life and he will still be regarded as one of the best to ever step up to the microphone. He has put together a run that has seen him become the king of New York, and his work on this track is one of his best. It was catchy, had the perfect music and came out at just the right time. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 7

Pick Or Pass “Ms. Jackson”

Straight from Atlanta, these Southern boys have been dropping heat since they were much younger men, and while there were a number of songs that would have been more than fine to include on this quiz, we decided to go with this classic track. It flexes a little bit of everything that the group can do, and it is one that we all know. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 8

Pick Or Pass “It Was a Good Day”

Should people find themselves having a day that serves as a break from the monotony of life, then this song is always fitting to play as a nightcap. Ice Cube was already a name thanks to his time in one of the most influential groups ever assembled, and his solo run would have a number of hits, including this song, which was essentially the cherry on top. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 9

Pick Or Pass “ZeZe”

The current state of rap is something that has been polarizing for many, but people unwilling to recognize a good song when they see it will always spout off nonsense. This song is one of the top tracks on the radio, and the gentlemen involved with bringing it to life have all been doing exceptional work. The beat is fresh, and the bars are a perfect fit. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 10

Pick Or Pass “In Da Club”

People seem to forget the type of impact that 50 Cent had when he signed with Eminem and released this track. Radio stations could not get enough of it, and 50 Cent would use his newfound fame to help a number of other performers get some radio play as well. When it comes to straight music, this song has one of the best beats in rap history. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 11

Pick Or Pass “Dance”

This man comes along and cranks out a hit just when it seems like people have put him on the backburner, and his ability to do this has been a huge reason why he has stuck around longer than most rappers ever will. He has a knack for creating music that is perfectly suited for the radio, and we imagine that he’s cooking up something nice right now. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 12

Pick Or Pass “All Eyes on You”

In recent years, many people have been seeing this man pop up in the media quite a bit, sometimes forgetting that he has done well for himself in the music industry. While his beefs are usually what grab headlines, we decided to feature one of his biggest songs on this quiz due to what it was able to achieve on the charts. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 13

Pick Or Pass “Hard in da Paint”

This song was everywhere when it was released, and the man responsible for making it a hit was able to take all the money to the bank after it became a massive success. He has been able to maintain a lucrative go of things since the song broke into the mainstream, and he has had some well-documented interactions with fans that have gone viral. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 14

Pick Or Pass “I Get The Bag”

This is one of the catchiest songs released in the last 5 years, and it is almost impossible to find someone that doesn’t love this song. While the lead on a song can do wonders, having the right feature can make all the difference, and to say that this song got that right would be a massive understatement. Talk about a truly memorable hit. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 15

Pick Or Pass “Blow the Whistle”

Who says an old dog can’t learn new tricks? Too Short had been in the game since before it was a radio fixture, and he was already considered a pioneer before he dropped this banger and reached out to a new generation of kids. He took his Bay Area roots and brought it to the masses once again, this time creating a memorable hit. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 16

Pick Or Pass “Who Am I”

When it comes to the history of the genre, there aren’t too many songs out there that are as essential as this one here. Southern California has been a massive reason why the genre is where it is today, and this man teamed up with just the right people to create what became one of the best songs in history. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 17

Pick Or Pass “Forgot About Dre”

The title of this song makes a statement without being brash, and the song was able to become a radio fixture without being annoying. Once again, Dr. Dre was able to bring perfect balance to a song, churning out one of the biggest hits of the era with one of the best to ever do it. It is an absolute must-listen for new fans. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 18

Pick Or Pass “Problems”

Sometimes, a song will come along that isn’t concerned with voicing a concern or conveying the problems of the youth. Instead, a song will sometimes look to be a little bit of fun, and this song was able to do just that when it came out. Its lyrics won’t blow people away, but it is a fun tune that hits the spot. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 19

Pick Or Pass “Sicko Mode”

Travis Scott knew that he had a chance to capitalize on a whirlwind of press and reach uncharted territories of success if he were to lead off his latest release with a banger, and when people finally got a taste of this tune; the Houston rapper reached the top of the charts and beyond. He is currently bigger than ever. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 20

Pick Or Pass “Get Low”

This song is an embodiment of the era in which it was released, and the people old enough to remember this song being on the radio are probably enjoying their 30s and reminiscing about a place in time when Crunk was all the rage. The song was inescapable when it was at its peak, and that was just fine for most people. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 21

Pick Or Pass “Gold Digger”

Kanye West used to be one of the premiere artists in the world, but his constant place in the media has led some to forget just how talented he actually is. He has a catalog of music that is as impressive as anyone else in the business, and his pairing with Jamie Foxx wound up producing a massive hit for fans. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 22

Pick Or Pass “Mask Off”

Sometimes, simplicity can be just what the doctor ordered, and we can guarantee that more people know all the words to this song than they realize. It turned out to be the exact thing that fans were looking for at the time, and its success would go a long way in the artist behind the tune reaching a new level of fame. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 23

Pick Or Pass “Black Beatles”

The men behind this song exploded onto the scene in ways that no one could have predicted, and when this track finally hit the radio, people knew that they were hearing the real deal. While impostors come and go like a thief in the night, these men came, saw and conquered, remaining hungry for more. This song remains one of their biggest hits. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 24

Pick Or Pass “Feels Like Summer”

Unless people simply haven’t been paying attention, this man behind this track is among the most famous in the world today, and not just for what he has done in music. He has shown himself to be a gifted comedian and actor over the years, and the fact that he is such an all around talent means that people will always wait and see what’s next. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 25

Pick Or Pass “No Role Modelz”

Bridging the gap between old and new can be hard to do, but the first words of this song did precisely that. Being a talented lyricist doesn’t always guarantee success, but the fact that this man has bars for days and can do so in an appealing way is a reason why he’s considered among the best of his era. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 26

Pick Or Pass “No Problem”

Despite the fact that this man is as gifted as any in the business today, many people know him for the recognizable hat that he wears. Being able to stand out in more than one way can go a long way for an artist reaching people, and this man is one of the most talked about performers around. He’s a legitimate talent. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 27

Pick Or Pass “Country Grammar”

The world simply wasn’t ready when this song was released, and thankfully, they were able to quickly catch on and help turn this song into a blockbuster hit on the radio back in the day. The man behind the song reach and incredible level of fame in no time, and he would continue to drop hits on the radio for years. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 28

Pick Or Pass “Bad and Boujee”

Not only was this song among the catchiest released in the last 10 years, but an incident at an awards show wound up turning it into a meme as well. The group that made this track has been reaching the top of the industry, and this was the track that truly put them over the top and made them stars. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 29

Pick Or Pass “Lose Yourself”

Eminem has more hits than nearly any rapper alive at the moment, and while there were tons of songs that could have been a good fit on this quiz, we went ahead and chose the one that did all the little things right. The music, lyrics and imagery of the song took the world by storm and made Eminem a legend. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 30

Pick Or Pass “Anaconda”

Sampling hit songs from the past can be a great way to put a fresh take on things and make a hit, and this song did that and more when it was released a few years back. Nicki Minaj was already popular when this song hit the radio, and it wound up being a colossal hit for the acclaimed rapper. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 31

Pick Or Pass “Started From the Bottom”

Drake is arguably the best in the business at the moment, and like King Midas before him, everything that he touches turns to gold. Even though Drake largely controls the radio, even he outdoes himself sometimes, and the impact that this song had upon its release was something that no one saw coming. It was a track that took his stock to another level. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 32

Pick Or Pass “Yonkers”

Tyler, the Creator has his own unique way of doing things, and this is largely why he has such a loyal following all these years into his run. Not only are his songs dynamic and unique, but the music videos for the tracks are just as captivating, and this video was largely talked about once it hit the small screen. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 33

Pick Or Pass “Whatever You Like”

T.I. has had himself an impressive go of things in the music business, and the fact that he has been such a success as a performer on the big screen has done wonders in him remaining relevant and loved by his fans. Though this track is chiller compared to some others, it was a massive hit for him when it hit the radio. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 34

Pick Or Pass “Gucci Gang”

Lil Pump is one of the most infamous people on social media in this day and age, and while many people are quick to point out that this song lacks an semblance of lyrical sophistication, it is a song that is as fun and as catchy as anything that has been released in the last decade. It helped him haul in tons of cash. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 35

Pick Or Pass “C.R.E.A.M.”

In Wu-Tang we trust. The Staten Island rappers dropped some classics back in the 90s, and many people consider this song the crown jewel of their discography. It paints a dark picture of life in a hard place, and it clues people into a world much different from their own. Wu-Tang reshaped the genre and showed the world what Shaolin was all about. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 36

Pick Or Pass “Humble”

Kendrick Lamar is one of the most talented men in the industry at the moment, and any time that he gears up to release a new record, people stop what they are doing to give it a listen. While his music has been eclectic over the years, he is not opposed to making some radio friendly tunes like this one. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 37

Pick Or Pass “Rack City”

Tyga has spent plenty of time in the headlines over the years, and it has caused some people to forget what he has accomplished in the world of music. The truth is that Tyga has taken over the radio multiple times in his rap journey, and this song was one that spent a considerable amount of time on the charts. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 38

Pick Or Pass “Can’t Nobody Hold Me Down”

Diddy has developed into a full on mogul over the years, but back in the 90s, he was a rapper from New York looking to cement his place on the radio. He had all the talent and the charisma to get the job done, and once this song took of and reached the mainstream, there was no looking back for the man. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 39

Pick Or Pass “Definition”

Musical pairings can yield mixed results, but Mos Def and Talib Kweli turned out to be everything and more when they linked up and formed the group Black Star. Though the group was relatively short lived, they were able to drop an album that changed the game, and that record featured this tremendous piece of music that is still as good as it ever was. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 40

Pick Or Pass “California Love”

Tupac is arguably the greatest rapper in history, and this song remains among the most famous that he ever made. Any young performer wanting to hone their craft will use Tupac as the measuring stick of talent. Even now, when this song hits the radio, people stop what they are doing to soak it all in. Yes, it is truly that great. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 41

Pick Or Pass “Young, Wild & Free”

Wiz Khalifa has been cranking out hits for a number of years now, and it seems like just the other day that he came from out of nowhere to take over the radio and become a star. This song is one that hit the radio at just the right time and was able to do some impressive things for the rapper, helping him cash in once again. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 42

Pick Or Pass “Crank That”

People can try to pretend all they want, but deep down, they know that they tried to do this dance at least once. While it is difficult to get the world to love a song and dance routine, the ones that are able to break the mold and do this successfully are the ones that wind up generating millions of dollars for the artist. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 43

Pick Or Pass “Get Back”

Even though he can more than hold his own on the big screen, the truth is that this man rose to prominence on the radio. He was able to have a number of massive hits that kept him at the top of the business for quite some time, and it is great to see that he was able to find a ton of success in another facet of the entertainment industry. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 44

Pick Or Pass “Rockstar”

Post Malone has been a phenomenon over the last 2 years, and people have grown to love this quirky musician thanks to his eclectic offerings. While he is an impressive rapper, he is also someone that can sing and play guitar as well, and this has helped him greatly when it comes to crafting songs that can fit on the radio. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 45

Pick Or Pass “X Gon Give it to Ya”

Thanks to being featured in a massively popular movie franchise, this song has become popular once again in recent years. The man behind this song was a popular rapper back in the day, and it seems as though many people have forgotten just how good he was on the microphone during the prime years of his run in the music business. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 46

Pick Or Pass “How We Do”

Southern California needed a fresh face to rise to the top and rep the area, and The Game was able to link up with 50 Cent to become the next big thing back in the 2000s. His debut album was one that took the world by storm, and it featured songs that told vivid stories about life in one of the roughest places in the state. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 47

Pick Or Pass “Work It”

Missy Elliott is a legend and pioneer of the genre, and the fact that people flip a lid whenever she takes part in anything just proves the type of impact that she has had over the years. This song is her most memorable, and people from all over the world have tried to decipher a very specific set of lyrics from this track ever since it was released. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 48

Pick Or Pass “Day ‘N’ Nite”

Kid Cudi is a legitimate talent that seems like he prefers hanging in the cuts and having a more personal connection with his audience. While he has been able to have success on the radio, it seems as though his releases are usually meant for a smaller, more compact following than for mass consumption. Nevertheless, this track was one that was too great to ignore. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 49

Pick Or Pass “Bodak Yellow”

Cardi B is the biggest thing in the world right now, and while she has done well for herself in the world of music, the fact that she receives an obscene amount of coverage from media outlets has helped her stay on top. People cannot seem to get enough of her, and she will be around for the foreseeable future. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

Question 50

Pick Or Pass “Thrift Shop”

It may seem silly now, but this song was all over the place when it was released. Not only did it catch on with rap fans, but there was a unique aspect to this tune that helped it catch on with people of all walks of life. It took over the radio and propelled its artist into stardom in the blink of an eye. Picking or passing this famous song will bring us one step closer to the big reveal waiting for each participant! (Billboard)

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