By Daniel Paiz

Hip Hop reached its 50th anniversary days ago on August 11, 2023. The culture, music, and art form has been redefining so many aspects of popular culture, and it’s finally front and center where it belongs. The culture and music aren’t without fault, ranging from ongoing misogyny to erasing parts of its history. Many including this writer think of the rapping and beats first, but the culture also includes the deejaying, the breakdancing, the graffiti, and doing the knowledge.

Some might include more pillars, but at its core the DJs, bboys and bgirls, graffiti artists and taggers, and MCs are what made this thing worldwide. There’s a lot that needs to be addressed, but there are some positives too. With more access to the tools and programs needed to make music, more people across the world are sharing their stories and narratives. It is impossible to hear everything out there, but one can certainly try.

This list of 50 songs is an attempt to share music from artists who might not be on your radar. The songs are not ranked, because that doesn’t matter as much as listening to what’s on the list. Plus, these are 50 tracks that this writer thinks folks should check out; if you have tracks you felt like were missed or you disagree with this list, by all means make your own and let’s compare. Having some healthy competition, sharing music, and building community are a few of the good things that hopefully outweigh the bad that keeps making headlines so often.

Cypher Sessions’ 50 Most Underrated Hip-Hop Songs

It is difficult to choose 50 songs because of the massive volume of stuff that is out there today. Pair that together with what’s been created over the past 50 years, and this is a journey of difficult yet enjoyable proportions. Each track will be listed with the artist’s name, (album or project), name of the song, and the (year) it was released. A brief description as to why it was picked follows as well. Here we go.

Danger Mouse & Jemini, ft. The Pharcyde (Ghetto Pop Life): Medieval (2003)

An unconventional bet for most, Danger Mouse does his thing to lay a sonic landscape for Jemini to throw down on. This project could be released in several different decades, and still sound fresh and new. Medieval isn’t done much in Hip-Hop, but these two do a solid job of keeping up the theme.

A Tribe Called Quest (Beats, Rhymes & Life): The Hop (1996)

The Hop is one of those album cuts that understandably gets slept on. A Phife Dawg wanting the smoke verse to end the track is unexpected but appreciated, especially for an ATCQ track. At this point in the ATCQ timeline, things were also starting to get a bit internally disrupted in the group. It wouldn’t be that big of a stretch to hear some frustration in these bars.

Lupe Fiasco ft. Nayirah (Drill Music in Zion): Precious Things (2022)

Lupe Fiasco’s method of perspective is something few others can rival. The attention to detail, the reflection of the mechanics of something as simple as hand movements, you don’t hear this kind of thought process very often. There’s the perspective as well of you view hand actions at a societal level as well as at a personal level; sit with that for a moment. Analyzing things from different levels like this can help to put together a bigger picture. Sometimes putting the picture together leads to tough reveals.

Rapsody (Eve): Nina (2019)

Nina is a fantastic song all on its own, but what puts the cherry on top for this song is that this is the opening track on Eve. Lots of rappers have skits, have an instrumental, seem to not always have something planned for the opener other than letting you know who you’re listening to. Rapsody did what not that many emcees are doing: hit the ground running from the jump. Arguably this is Rapsody’s best project to date, and this song is a snippet of why. The lyrics are on point, the bars build a picture, and you are getting an idea of what to expect from the moment you press play. Rapsody is not an artist to be slept on, and Nina is a track that is slept on by far too many.

Supaman ft. Acosia Red Elk (Illuminatives): Why (2021)

Supaman has been creating beats and rhymes for some time now, and he does a solid job of combining traditional and contemporary viewpoints in his work. Hip-Hop from Native American and First Nations artists doesn’t get enough buzz. Ideally songs like this one that are timeless and relevant can change that. This is one of those tracks that you can play on repeat and reflect on something new each time.

Rapsody (Laila’s Wisdom): Laila’s Wisdom (2017)

Rapsody has a fluidity to her rhymes that stands out amongst the myriad of artists out there. Her beat selection is fantastic, and those punchlines mixed in with the overall narrative is memorable for this listener. In case you were wondering, this is also the opening track for this respective album. There are artists who are giving this level of rhyme on their heavily promoted singles, so this brief taste of sound might just pull you in if you want to see the range Rapsody has.

Blu & Exile (Miles): You Ain’t Never Been Blue (2020)

Blu & Exile are Hip-Hop’s dynamic duo that somehow has been under the radar to larger popular audiences. Blu delivers verses few are crafting, and Exile might be a top three producer who can also rap. Below the Heavens is the project Blu & Exile fans flock to, but Miles has tracks that play the rest of your evening without any need to find something else to play. This track is one of those classic Hip-Hop everyman songs, where what’s lacking for someone shapes them just as much as what they possess in the moral or material world.

The Reminders (Born Champions): If You Didn’t Know (2012)

There’s a lot to talk about when it comes to Aja Black and Big Samir, better known as The Reminders. The chemistry between these two, the rhymes that pack a punch and get you moving, and the subject matter is just so good. Both have a one of one sound, and when paired together there’s really nothing else out there in Hip Hop that seems similar to these two. Samir can from time-to-time sneak in some verses in another language, while Aja will sing her heart out and grab all of your immediate attention. Denver and Colorado often aren’t credited as hubs of Hip-Hop, but The Reminders are one of several acts that will make you rethink that assumption.

Sa-Roc ft. Black Thought (The Sharecropper’s Daughter): The Black Renaissance (2020)

Black Thought is a tough emcee to keep up with, but Sa-Roc does so and volleys some rhymes back to see if Thought can keep up. When lyrical steel sharpens steel, the audience wins, and this track is one too many slept on. This tends to happen to women who rap and have this level of rhyming dexterity. This isn’t to say women who rap are should deliver a certain way, but rather that there are women who can rap every bit as good as whoever else is in the booth.

The Roots ft. Dice Raw (Undun): Lighthouse (2011)

The Roots have a catalog any other musical act would envy to dream about having. Part of crafting such a comprehensive discography is delivering thoughtful pieces that deserve pondering and sitting with a song in the space it provides. Reflection of what you’re hearing can increase one’s appreciation, and giving some time to revisit a Roots song is never a bad use of time.

Killer Mike (R.A.P Music): Reagan (2012)

A big part of Hip-Hop is getting information out to the masses, and that includes messages about politics and history. A key contributor to Hip-Hop once said (paraphrasing here) that this music is created by those living in a world of lack. Information is power, and learning about the sins of the past can help one to avoid repeating them. Killer Mike on no uncertain terms tells you about both Reagan but also the structure in place the United States has in terms of power. This is a huge part of what Hip-Hop arose out of and to say otherwise is to ignore the foundation of this culture and music.

Run the Jewels ft. Pharrell Williams & Zack de la Rocha (RTJ4): JU$T (2020)

Run the Jewels is usually good for a good critique of the current sociopolitical landscape listeners are witnessing, but this one gets that extra push with RATM’s Rocha. Nearly everytime Rocha is on a Hip-Hop track, he does his thing and then some. Mix in some Pharell vocals and you have a piece of work that gets stuck between the earlobes rather quickly.

N.A.S.A ft. David Byrne, Chuck D, Seu Jorge, Ras Congo, Z-Trip (The Spirit of Apollo): Money (2009)

Artists from North America and South America (NASA makes more sense now right) were brought together by two DJs to make this fantastic album. One of the best tracks is Money, and it feels like somebody took Public Enemy and added a bunch of people to their song. This track is layered with different sounds and different voices. The overarching critique from this song has what long-lasting music possesses: that wonderful balance of being both timely and timeless.

Big Freedia (3rd Ward Bounce): Rent (2018)

New Orleans Bounce music is one of those regional subgenres that is far too slept on. There is not a lot out there right now that has this kind of energy and movement involved. Big Freedia boosts the mood on whatever track they’re on, but this one is a pretty good introduction to their music. Freedia creates music that’s welcoming to anyone listening, despite how Hip-Hop has routinely been quite the opposite when it comes to LGBTQ artists. That’s slowly changing, thanks in part to artists like Big Freedia.

Blue Scholars (Oof! EP ): Hi 808 (2009)

Seattle Hip-Hop doesn’t get a lot of recognition, but there’s a solid scene in the SEA and the northwest in general. Blue Scholars are one of those groups that deliver fun and thoughtfulness all at the same time. This beat will become an earworm for you, and the fellas might make you rewind a few lines to make sure you heard what they’re dropping.

Blue Scholars (Cinemetropolis): George Jackson (2011)

Blue Scholars have that knack of being able to go from fun and lighthearted thoughtfulness (see previous song) to digging a bit deeper. Cinemetropolis as a complete body of work balances fun and reflective quite well but tracks like this one stands out for several reasons. There’s a catchiness on the surface, that then reveals the declaration being made in the chorus. Sometimes one has to resolve to do something, even if that promise is spoken to oneself initially. That’s where all change starts, with the self.

Braille ft. Toni Hill, Tony Stone (Shades of Grey): Shades of Grey (2004)

Another rapper in the Northwest, Braille hails from Oregon, somewhere not far from Portland. The Christian rapper delivers his takes on life and Hip-Hop through that lens but doesn’t preach or push anyone towards religion. Rappers like Braille, LeCrae, and Dee-1 are all pushed towards the margins of Hip-Hop because of their ties to religion (in this case Christianity). However, like other groups on this list not given their props, they are bringing up interesting commentary and solid verses to check out.

Lyric Jones (Closer Than They Appear): Want to Say (2020)

Lyric Jones is one of many women out there making such good music and deserving more listens and more attention. The beats are so good, the lyrics are solid, and this track is one of many that can and should stay on repeat. This very much sounds like something that could’ve come out of 9th Wonder’s camp, which is quite the accolade because it’s difficult to recreate that kind of soulfulness.

Rah Digga (Dirty Harriet): Break Fool (2000)

Rah Digga is one of those emcees who was and still is somewhat slept on. The bars are better than a decent amount of stuff out today. The good news is, it’s never too late to get familiar with Rah Digga and other women who have a plethora of tracks to check out.

DMX (It’s Dark And Hell Is Hot): Stop Being Greedy (1998)

DMX was on fire when he put out two albums within one year of each other. There are definitely a number of other jams that come to mind before this one, but this one feels like peak X. The energy, the rhymes, the beats were all turned to 11, but this track reveals a bit of X’s thoughtful side.

Run DMC ft. Pete Rock & C.L. Smooth (Down with the King): Down with the King (1993)

A clashing of two historic groups, Run DMC featuring Pete Rock and CL Smooth seems like a dream match that unexpectedly happened. The instrumental is so 90s, the chorus is too, and all of the verses feel like each emcee is at their best. It’s surprising that this track doesn’t come up more when Run DMC is written about or discusses.

De La Soul ft. MF DOOM (The Grind Date): Rock Co.Kane Flow (2004)

This is one of those hype tracks that until you hear it in full, you likely don’t realize that’s what this is. De La Soul does a great job of building the energy in each verse, leading to DOOM throwing down. This track live is also a whole lot of fun, as I experienced all three members of De La thrown out some choreography that was unexpected but very fitting for this song. This group isn’t really known for hype or high energy jams, but it adds to the overall concert experience.

Snow Tha Product: Bilingue (2019)

This iteration of Snow has found her niche. Reggaeton and Spanish music in general have become more popularized over the past decade, which has led Snow to dropping a lot more rhymes in Spanish. The audience is there, and this is one of those tracks that reminds listeners what Snow can do.

Krizz Kaliko ft. Snow Tha Product (Neh’Mind): Damage (2012)

Snow Tha Product earned her stripes as for years and years she worked to gain fans from the underground Rap scene. Snow largely seemed to get some traction with Tech Nine and Strange Music fans, due to her ability to speed rap and drop witty bars that easily rivaled and sometimes surpassed Strange Music rappers. Compared to her 2019 entry on this list, Snow put everything on the line to gain that support. English listeners missed out, because with the rise of Reggaeton and popularization of rap tracks in Spanish, Snow has little reason to pursue English listeners at this time. Krizz did Krizz Kaliko things, showing why he was Tech’s number two artist on Strange for so long; few at the time of this video release would’ve predicted the meteoric rise Snow has had, while Krizz has faded away.

Che Noir (After 12): Divine Knowledge (2020)

Che Noir has that sound of someone who has been doing this a long time. Not every rapper sounds like they’ve worked their way through rap cyphers and underground showcases, coming out on the other end even better than before. Che sure does though. That kind of sound is crucial for Hip-Hop.

Big K.R.I.T (K.R.I.T IZ HERE): Make It Easy (2019)

One of the cooler tracks from KRIT in recent years, this song is smooth both on record and live. There’s a throwback feeling of sorts when this song plays. That feeling pairs quite well with the verses and asks to be replayed with how well the entire track moves through your speakers. Perhaps the old school Jazz lounge feel also pulls this listener in, as this one never gets old.  

Big K.R.I.T (Digital Roses Don’t Die): Rhode Clean (2022)

There are a couple of tracks on this list that give you a different viewpoint, and this one gives you an idea of the viewpoint from one’s ride. It’s not as intricate as Lupe’s Precious Things, but it is something you don’t hear that often. Plus, with how intertwined car culture is with Southern Hip-Hop, it’s kind of surprising there have not been more tracks like this one. The smoothness, the gliding lyrics throughout, this is one of several Big K.R.I.T tracks that are under the radar for far too many Hip-Hop fans.

Mumu Fresh (The Reintroduction of Mumu Fresh): Stay (2014)

Maimouna Youssef, also known as Mumu Fresh, has been dropping thoughtful and intriguing lines for quite some time now. Mumu has the bonus combo of being able to both sing and rap quite well. This combo definitely helps this independent artist, which is a hard path to take. Fresh continues to make new music and this particular track has stuck with this listener. The balance between her storytelling abilities and just how fun the track sounds is so smooth.

Brother Ali (All The Beauty In This Whole Life): Dear Black Son (2017)

This powerful track is Ali breaking down how childhood is robbed from Black sons and how police forces choose to not see who is in front of them but instead what they’ve been taught to see. There’s an honest and thoughtful tone from Ali throughout this track, reminding listeners what still goes on today. This is one of those Hip-Hop tracks that bridges the gap between timely and timeless. Six years ago this was released, and it sounds just as relevant today.

Brother Ali (All The Beauty In This Whole Life): Own Light (What Hearts Are For) (2017)

While Shadows of the Sun or Mourning in America and Dreaming in Color likely grab one’s attention when first listening to Brother Ali, there’s a few tracks from the newer albums to check out. Ali can switch effortlessly between something political and heavy to something energizing and unifying. Own Light (What Hearts Are For) is his quintessential song of openness and coming together; it’s also a track you will hear nearly every time he performs. Brother Ali fans know this song is a staple, but the larger Hip-Hop community might not be as familiar.

Aesop Rock (The Impossible Kid): Dorks (2016)

There are few rappers out there as wordy and vivid as Aesop Rock is. What’s also nice is, Rock throws things back to the days where a chorus isn’t the most important part the song. The mastery of describing the moment, whether mundane or memorable is a one-of-a-kind feat by Aesop’s rhymes. To complain about “how wordy” these verses are would ignore the wordsmithing accomplished here.

Aesop Rock (Spirit World Field Guide): Kodokushi (2020)

Spirit World Field Guide is the first album I’ve encountered from someone not named Lupe Fiasco that I have to listen to the entire thing before I can maybe know what’s going on. This track stands out to me first from this project because of the imagery, as well as the word choice throughout. There are some graphic lines here, but also some visually intriguing lines flowing along as well.

CZARFACE ft. MF DOOM, Del The Funky Homosapien (Super What?): Jason & The Czargonauts (2021)

CZARFACE is a group that utilizes comic book characters and references into pop culture and storytelling narratives throughout their work. Every album has a comic book design for the album cover, and each one feels like a throwback to an earlier time. This track stands out not only because of the features, but the production also places you in panel after panel. Comic book rap isn’t really a thing, but these guys could easily guide the potential subgenre if they chose to.

Madlib & MF DOOM (Madvillainy): Accordion (2004)

A duo that often gets overlooked in more mainstream conversations, Madlib and MF DOOM worked so well together. It makes sense, as both artists sound as if they can make anything at any time. This is one of those tracks where it seems like as the listener, you would want this to be a longer song. However, the duration heard works so well it’s likely it wouldn’t be such a standout if it wasn’t created as it was.

Gang Starr (Moment of Truth): You Know My Steez (1998)

Gang Starr has long been slept on when it comes to reflecting on Hip-Hop’s best acts. Perhaps it’s the monotone delivery from Guru, perhaps it’s how underrated DJ Premier is by those outside of the realm of underground Hip-Hop. Either way, this track isn’t one that first comes to mind when Gang Starr is mentioned (Moment of Truth, Work, Mass Appeal, and Above the Clouds often get listed first).

OutKast (Southernplayalisticcadillacmuzik): Ain’t No Thang (1994)

The debut OutKast album had some songs on there that still feel like the it’s the very first listen. The sound of the equipment getting ready to play the track, the sound of the tape winding along as the music drops, it puts you in the setting of where these two are rapping. Almost like the listener is in the basement where the Dungeon Family records and chills. That’s something you don’t get as much on a consistent basis, that feeling of being in the room where the music is manifested.

Outkast ft. Morris Brown College Gospel Choir (Stankonia): B.O.B – Bombs Over Baghdad (2000)

OutKast’s ability to combine slick rhymes with otherworldly bass (courtesy of Organized Noize and other affiliated DJs and producers) was one of many reasons this duo helped put Atlanta on the map. This particular song was initially about the music industry but gained popularity during the height of the War in Iraq in the early 2000s. The frenetic beat and rhymes draw the listener and doesn’t let go.

Masta Ace ft. Pav Bundy, Hypnotic Brass Ensemble, Chuck D (The Falling Season): Young Black Intelligent (2016)

Born to Roll and Sittin’ on Chrome are likely the two first tracks veteran and new fans of Masta Ace first hear, which makes sense. They’ve been around since the 90s and are tracks you still might hear from time to time. However, this selection is on this list because it has a different kind of longevity to it, one that’s memorable due to the lyrics before the beat (and not vice versa). Also, this was my introduction to Masta Ace, and this version is the one I’ve heard more than the 90s version (both are very underrated).

Metro Boomin ft. A$AP Rocky, Roisee (Metro Boomin presents Spider-Man: Across the Spider-Verse): Am I Dreaming (2023)

Metro Boomin isn’t someone that comes to mind when discussing underrated music, primarily because anything he makes grabs attention of the entire music world. However, this song at the beginning of the end credits for Spider-Man: Across the Spider-Verse encompasses the entire film into one song. Every emotion you witness and experience throughout the film appears here. Songs that do that are powerful, and a major part of this music and culture is storytelling. Newer artists also aren’t given much slack, which has been happening to this culture for its entire existence.

Eric B. & Rakim (Paid in Full): As The Rhyme Goes On (1987)

Eric B. & Rakim are peak 80s when it comes to demeanor, beats, and rhymes. Rakim uses his Jazz background to drop rhymes that today not many can rival, while Eric B. puts together sounds that encapsulate an era. Paid in Full is a classic album, and there are a few joints that get overlooked because of I Ain’t No Joke and the title track of the same namesake. Rakim is definitely one emcee all others should study and learn from.

Residente ft. Ibeyi: This is Not America (2022)

2023 is a good time for all Hip-Hop fans to remember that this culture and music isn’t just in English or just in the USA. This thing is global, and a lot of places around the world are using it as a tool. Puerto Rico’s Residente, one of the founding members of Calle 13, has rapped to listeners a perspective not often given in mainstream Hip-Hop. There are places outside of the United States that have traditions and cultures to learn from, and Residente is one of many delivering messages that are universal in nature.

Ana Tijoux ft. Jorge Drexler (La Bala): Sacar la Voz (2012)

There are lots of women outside the US and speaking other languages who are sharing their messages via Hip-Hop. The Chilean-French singer and rapper Ana Tijoux has been one of those voices for decades now, and someone likely flying under most Hip-Hop radars. This track focuses on utilizing what everyone has, and that’s your voice. 1977 tends to be the track most fans of Tijoux point to for an introduction, but this one feels like a better starting point for this fan.

J Dilla (Donuts): Time: The Donut of the Heart (2006)

It is very possible that this J Dilla song that clocks in at under two minutes is not all that underrated, but it is the first jam I think of by James Yancey. There are so many Dilla joints, and so many artists that he worked with that make it hard to only choose one song. Those who fashion themselves scholars of the late great producer likely have a few tracks they immediately go to. For this listener, selecting my favorite Dilla track seems like a good way to tease newcomers to the Detroit producer’s discography.

Felt (Atmosphere + Murs) (Felt 4 U): Never’s Enough (2020)

While I’ve been a longtime fan of Murs, the past five years or so are when I became a very big Atmosphere fan. Putting these two acts together is always a treat, and this one is no exception. Around five or so into the COVID pandemic, this album dropped, and this song in particular gets played nearly monthly. The funky smooth production from Ant, the everyman rhymes from Slug and Murs, it all fits together like a puzzle. Hip-Hop has hit 50 years of existence, and middle-age is going to require some artists like these to remind everyone that life rolls along.

Lyrical Landlordz (The RAP Agreements): Where The Party @!!? (2019)

Hip-Hop will often suggest to think global and act local, and there are some Denver and Colorado acts that deserve some shine. One such group would be Denver’s own Lyrical Landlordz, comprised of Sonny Nuke, DENT, and DJ Paulen. The boom bap inspired track displays bar after bar from Sonny and Dent, and Colorado is well represented by this group. These guys have played all around Colorado and have also played across the US as well, and independent acts like these are crucial for the culture and the genre.

Wretch 32 (FR32): Time (2017)

Grime is one of those genres to me that’s a relative of Hip-Hop, kind of like a younger cousin or something. It’s a uniquely UK sound, and one that’s been around my headphones since the early 2000s. Dizzee Rascal, Tinie Tempah, Stormzy and more have gotten most of the exposure, but there’s a whole lot more than a few who have had crossover success. Wretch 32 comes to mind in this instance, as he can go through the gauntlet in terms of sounds and subject matter. This track is one of those that highlights Grime beyond the heavy bass and club themes often stereotyped with this music.

Denise Chaila (GO Bravely): CHAILA (2020)

The Irish emcee has less Grime and more fluid flow throughout all of her music, and it works so well. Ireland is not a place one thinks of when it comes to Hip-Hop, but this culture is worldwide. Denise Chaila is newer to the rap game but has played in front of large crowds. Chaila has that deadly combo of charisma and bars that will grab your attention.

Jay Rock (Redemption): ES Tales (2018)

Rhymes about one’s reality and surroundings are a huge part of this genre, and there a lot to pick from. Jay Rock’s ES Tales has an authentic feel to it because everything in this song feels like it’s presented as is, documentary-style. The beat helps with both Rock’s verses as well as the video itself.

Little Simz (Sometimes I Might be Introvert): Fear No Man (2021)

Little Simz has been blowing up over the past couple of years, but it seems like not that many people in the US are checking her out. Perhaps the UK artist is considered Afrobeat and not Hip-Hop, but this fan considers Simz to be part of the culture and a voice that Hip-Hop needs. The bars dropped on this evermoving beat flow so well, and there’s a yearning to hear more even after the track finishes.

clipping. ft. Cam & China (Visions of Bodies Being Burned): ’96 Neve Campbell (2020)

Hip-Hop has a wide range of subgenres, and one of them can sometimes be dark. clipping. didn’t start as a horrorcore rap group and still isn’t necessarily one, but this song and this album were their choice to make in that vein. The word choice from this group and descriptors are top-tier, and the production enhances everything you hear. Daveed Diggs might’ve gotten your attention on the stage, but he can certainly keep it with his rap group as well.