Just before the release of Big Sean’s fourth studio album I Decided, Jay-Z gifted him a Roc-A-Fella chain, and in that moment the fate of the kid who secured a record deal from bum-rushing Kanye West at a Detroit radio station was effectively solidified among the stars, because as Jay-Z said himself, Sean earned it. He earned all of this with painstaking leg work. Big Sean has been rapping like he has something to prove since well before he signed a deal with G.O.O.D. in 2007 and 10 years later, he is one of the biggest mainstream rappers in the game, and its all due to his professional consistency and drive.

Since his days as a high school student in the motor city, Sean Michael Leonard Anderson took his craft ever so seriously and took advantage of any and every opportunity to showcase his skills. He got his start in weekly Rap Battle clashes for Detroit Hip Hop Station WHTD, and built a valuable relationship with the station that would help him connect with Kanye West in 2005. Then, in 2007, shortly after he signed his deal with G.O.O.D. Music, he released his first official mixtape Finally Famous: The Mixtape, and it quickly infiltrated the hip-hop blogosphere, becoming a defining mixtape of that era. Fast forward, eight years later, and he scored his first No. 1 album with Dark Sky Paradise, and took command of the game with hits like “IDFWU” and “Blessings.”

Now it’s 2017, and Sean Don is still riding the wave, and creating it, following his fourth studio album, I Decided. This list is a representation of his growth (albeit not chronologically), dominance and patience with regards to the process. This top 25 should feel a bit like a time warp, depending where you stop in it, you’re taken to different stages of his ever-evolving career, but one thing that remains true through out, and should become evident with this list, is Sean’s relentlessness. If something didn’t hit the way he wanted it or expected it to– we’ve witnessed it through out the years–  he’d just dust himself right off and go back to the drawing board, never holding in any bitterness, constantly looking for positivity. What’s even more impressive about Sean’s rise to the top is how committed to holding down D-Town. As much as this is about celebrating the expansive discography, Detroit deserves some glory too.

4th Quarter

Top 25 Best Big Sean Songs of All Time

“4th Quarter” is an unprecedented showing of Sean’s skill set and combines both the old “on the come up” style of Big Sean with the new dominant and distinguished era of Sean into a heavenly, yet gritty, masterpiece.

With respect to the timeline of this release, “4th Quarter” along with “1st Quarter” and “Jit/Juke” were released just before Sean’s 2015 album Dark Sky Paradise which is one of his better commercial showings. So in a sense, songs like “4th Quarter” marked the beginning of the level-up the young G.O.O.D. MC embarked on.

Desire, Want, Need

Top 25 Best Big Sean Songs of All Time

From day one, Big Sean has always had big dreams and an even bigger vision. One of the main factors that attract so many to Sean and his music, is how genuine and aware he is anytime he jumps on the record. “Desire, Want, Need” is a very early representation of Sean’s forthcoming mantra and unquenchable thirst for greatness.

This one is really a nod to his veteran songwriting ability as we hear him masterfully weave his desires, wants and needs cohesively in and out of playful metaphors and aphorisms. It’s a staple from his mixtape catalog.


Top 25 Best Big Sean Songs of All Time

It’s almost mind boggling to think that we are just a few weeks past the five year anniversary of Big Sean’s Detroit mixtape, but it’s true. On September 5th, 2012 the project was unleashed, a return to form following a lacklustre debut album.

This mixtape was without a doubt a strengthening effort for Sean. “RWT” is like no other weed song to exist because it goes hard, like ridiculously hard, in the name of Mary Jane, and also in the favor of stunting.

Control Feat. Kendrick Lamar & Jay Electronica

Top 25 Best Big Sean Songs of All Time

When Ice Cube’s “No Vaseline” NWA diss was released in 1991, it spawned a grueling battle between Ice Cub and his former group NWA, and their manager Jerry Heller over royalties. Big Sean’s “Control” pushed the button in the game to initiate a free for all much like Ice Cube’s “No Vaseline” did in 1991, although, it wasn’t necessarily because of Sean’s verse, as we know.

The blatant blows from Kendrick Lamar and the intricate workings of Jay Electronica became the focal point when this song was released, a leftover track that didn’t make the Hall of Fame album. Still, let’s appreciate Sean for crafting this record and forcing artists to step their game up.


Top 25 Best Big Sean Songs of All Time

Another highlight from the Detroit mixtape, “Higher” is the hazy hyperreal verbal assault that prioritizes the ascent over notoriety within the come up. Key Wane provides the spacious and slumping production for this introspective rap ballad, that finds Sean airing out all of his inhibitions, apparently having a guttural urge to shit on the industry. When Key and Sean link it’s always ridiculously dope and this record is no exception.

Next time you feel like stunting on some haters and level up in this world let this track be your theme song.

Fat Raps (Remix) Feat. Chuck Inglish, Asher Roth, Chip Tha Ripper, Dom Kennedy & Boldy James

Top 25 Best Big Sean Songs of All Time

Finally Famous: Vol 3 was a defining project for Big Sean and featured several of his fan-favorite cuts. The project also housed a handful of standout features from the likes of Mike Posner, Curren$y and more. “Fat Raps (Remix)” is one of those moments that brings together some of the most important rappers who came up around the same time (we’re talking ’09 and ’10), for a shining array of styles. All of these guys kill this record — who steals the show, though?

Five Bucks Feat. Chip Tha Ripper & Curren$y

Top 25 Best Big Sean Songs of All Time

Once again we’re on Big Sean’s 2010 mixtape Finally Famous: Vol. 3. It featured a verse from almost anyone that was relevant, and even more so it featured a range of music that could satisfy almost any fan. So of course, there is a record on here for all of the stoners out there. “Five Bucks” is the perfect remix to the classic Luniz anthem “I Got Five On It” and showcases a staccato-like flow from Big Sean, which wasn’t one we’d hard a lot of at the time.

The added force from Chip Tha Ripper and Curren$y’s guest verses make this one a must have.

What You Doing

Top 25 Best Big Sean Songs of All Time

Easily one of Big Sean’s most widely known songs “What You Doing” is probably the best showing of Big Sean’s trademark flow and affinity for playful and memorable hooks. While the song is very evocative of his early discography (I mean, it was originally part of the Finally Famous Vol. 3 mixtape too), this song pushed genre boundaries and offered fresh experimentation, helping to cement Sean as one-to-watch.

This track is cocky, confident and witty and that is what Big Sean is all about. But what’s possibly the greatest thing about this record is that it asks the most important and pressing question, “Fuck You Doing?”

Mula Feat. French Montana

Top 25 Best Big Sean Songs of All Time

Big Sean’s Detroit had notably diverse range of producers. The standout, financially-conscious banger, “Mula,” allowed producers Young Chop and Bandcamp to galvanize Big Sean in a way that highlights his flow’s intensity like never before. Sean Don really turns up on this record as he prioritizes money over everything, it makes you want to do the same– or at least, get on your grind.

This song was literally so lit that Sean had to add a remix on his 2013 Hall Of Fame album, with the added support of 2 Chainz, Meek Mill and Early Mac. Which version goes the hardest?

How It Feel

Top 25 Best Big Sean Songs of All Time

Jiggy, groovy, jive, electric, however you describe this Detroit song, you’re most likely right, because it is so many things (including magical). “How It Feel” has this wild and soulful energy to it that certainly helped boost this tape and also define Sean’s roots. When this record comes on you want to dance and sing along; it’s easy to get swept up into the fast-paced two step soul of this track.

The trailer Big Sean did with this record for the tape basically nails the visual fantasy of a lavish life the song portrays. Who knew one could stunt and brag about the swag in such an outta-sight way.

Beware Feat. Lil Wayne & Jhene Aiko

Top 25 Best Big Sean Songs of All Time

Big Sean and Lil Wayne make a really dope pair, but it’s Big Sean and Jhene Aiko that are really the dynamic duo and it shows on their early collaboration, pre TWENTY88 days,”Beware.” Per usual, Wayne bodies his verse, but in all honesty it’s really Big Sean and his future TWENTY88 counterpart and girlfriend Jhene Aiko, steal the show.

The way these two harmonize is so beautiful and trance-inducing. This was also one of the first times we heard Sean Don and Jhene Aiko together so in a way, this song is incredibly special to Sean’s discography and likely his personal life too.

Bigger Than Me Feat. The Flint Chozen Choir & Starrah

Top 25 Best Big Sean Songs of All Time

With I Decided, Big Sean took the fate of his career into his own hands and assured both himself, his fans and the industry that he wasn’t going anywhere for a long time, and on top of that, that he would continue to rep D-Town until the end of it all. “Bigger Than Me” is more than the album outro, it’s Big Sean’s existential realization that material wealth isn’t necessarily the goal, as much as it is a perk, and what’s more, that Detroit is forever his home.

This record is so special for a number of reasons including all of the recent economic and environmental troubles impacting the state of Michigan. 

Halfway Off The Balcony

Top 25 Best Big Sean Songs of All Time

Big Sean’s I Decided is as much about the rapper being real with himself as it is about being real with the industry, and the track “Halfway Off The Balcony” perfectly synthesizes that relationship between Sean’s “real” self and his public persona. As he utters the chilling hook, “I’m hanging halfway off the balcony, over thinking cause my job is way more than a salary / Everything around me go like I just practiced / Alchemy, I realized when it come to girls that / Chemistry means way more than / Anatomy, she mad at me” we begin to understand that he’s gone through a bit of a learning curve over the past several years.

This record is overtly real, but what else do you expect from Big Sean? Also, the video for this track is on a whole other wave, so enjoy.

All Your Fault Feat. Kanye West & Roscoe Dash

Top 25 Best Big Sean Songs of All Time

Other than his first big hit, “Marvin & Chardonnay,” the Kanye West-assisted “All Your Fault” is the most important collaboration between Big Sean and Kanye West. This track gave Dark Sky Paradise a sort of energy that is unmatched by the daunting tracklist, which also boasts features from the likes of Partynextdoor, Chris Brown and more. That electricity is partially due to the outstanding production trio of DJ Mustard, Mike Free and Kanye West.

On the other hand, both Sean Don and Ye spit ridiculous bars on this record. You just can’t overlook this one. Kanye has always cosigned his pupil but this track proved his approval and appreciation of Big Sean, 100 percent.


Top 25 Best Big Sean Songs of All Time

This song is lit and probably the hardest banger in Big Sean’s catalog. By the way he spit on this record, it isn’t that hard to believe that Sean is working from 10 to 10 on that flow. We’ll let this record do the talking for itself.


Top 25 Best Big Sean Songs of All Time

If there is one thing we have all learned about Big Sean over the years it’s that he can maneuver his way through this game like none other. So it’s definitely fitting that one of his biggest singles is motivated by the motion.

Big Sean’s “Moves” is a straight-forward anthem for all the movers and shakers in this world.

High Rise

Top 25 Best Big Sean Songs of All Time

Big Sean’s “Supa Dupa” flow is absolutely ether and every go around he seems to show us that he can reinvent the flow in some newer and more fascinating way. “High Rise” is one of those points where we can hear the progression of the flow. 

It’s songs like “High Rise” that make Finally Famous: Vol. 3 such a historic and respected mixtape.

Paradise (Extended Version)

Top 25 Best Big Sean Songs of All Time

One could think of Big Sean’s “Paradise” as the segway into his new and improved style that calls for him spazzing on any and everything he gets his hands. To be fair, Mike WILL Made-It did provide the most thunderous backdrop, but it is Sean who truly conquers this beat with his ferocious and uncut flow.

Plus this song is dope, because we get to imagine a paradise that includes wearing a whole lotta ice and bedding the baddest of women.

Blessings Feat. Drake & Kanye West

Top 25 Best Big Sean Songs of All Time

This tracks line-up feels like the good ol’ days back in 2008, when Kevin Garnett, Paul Pierce and Ray Allen won the NBA Finals. Hell, this record is so good, one could compare the line-up to the original big three era of Larry Bird, Kevin McHale and Robert Parish, but that’s another conversation for another day.

Long story short, Sean, Drizzy and Ye killed this track, and it was equally a blessing as fans, to get to hear all three on one track for the first time. Praise God, for we are thankful, but Sean you think we can get a “Blessings Pt. 2” on the next LP?

Bounce Back

Top 25 Best Big Sean Songs of All Time

No one takes an L like Big Sean, and that’s a fact, because he is essentially the new age innovator of rebounding efforts. When “Bounce Back” dropped it literally blew up over night, and rightfully so, because the record is so authentic and accountable in a way that says, “Screw you if you think this L is going to defeat me.”

The way that Big Sean has utilized his career discography to champion sounds of motivation and positivity is refreshing, and it definitely plays a part in his appeal. Also, it’s a major reason why this song is essential.

Too Fake Feat Chiddy Bang

Top 25 Best Big Sean Songs of All Time

Every artist has that early defining hit that helped them build their reach and define their audience on the come up, and for Big Sean, that record is probably “Too Fake.” In a sense, this track helped to put Sean on the map in 2010 and gave him the outlet to a broader audience to view his work. Chiddy Bang is not only featured, but 1/2 of them produced the song (Noah Breakfast, then going by Xaphoon Jones), using a sped-up sample that was all the rage at the time.

Again this one appeared on the classic Finally Famous Vol. 3 mixtape.

Voices In My Head/Stick To The Plan

Top 25 Best Big Sean Songs of All Time

Flat out, this song is epic. To be honest, or more accurate, it’s like a mildly Schizophrenic roller coaster that almost everyone can relate to. The deafening inner dialogue driving you to “Get your shit together” coupled with the conscious prompts to stay grinding and to stick to the plan is the utmost sincere thing Sean has ever laid on wax.

Plus the switch up on this track is crazy, and takes you from being in your feelings to utterly hulking out to the crazy rhythm of the second half. It’s one of the best songs off Sean’s latest album.


Top 25 Best Big Sean Songs of All Time

This record will go down in history as one of the best break-up songs, and it’s probably because of how petty it is. Almost everyone can relate to the feeling of wanting to curse your ex, or any adversary, the fuck out, and Big Sean basically does it for you, you just need to press play.

Everything about this track is cinematic from the first drop to the angelic switch brought to life by the heavenly voices of the Choir sample, and even the High School-musical style music video that features Coach Kanye at the helm of a football team, lead by the All-American QB Sean Don. This one goes out to all the fuck bois and lame hoes we all have ever had the displeasure of dealing with.

Getcha Some

Top 25 Best Big Sean Songs of All Time

“Getcha Some” is cited as being Big Sean’s first big hit and helped propel him into the spotlight in 2009, as a guy everyone should keep their eyes on. This record exudes swag, like literally oozes it and it’s easy to see why Sean is so likable from this early banger, that appeared on his first Finally Famous mixtape, as well as the second instalment/compilation UKNOWBIGSEAN.

Everything about this track is on point from the bouncy production to Sean’s bars about his expensive tastes and the dickriders jocking on road. This is definitely an early essential for Big Sean, and should take you back to ’09 right quick, when the blogsophore was still on the rise, a much simpler time.

Supa Dupa

Top 25 Best Big Sean Songs of All Time

Big Sean is known for establishing, or being a harbinger at the very least, of the “Supa Dupa” flow, also known as the “Hashtag” flow, it utilizes a sort of call-and-response style with one word punchlines responding to the preceding bar. The title of the flow, of course, get its name from this particular song.

Sean gives us fair warning in the beginning of this track to prepare for the new dynasty, led by he himself. 

This record isn’t only about the “Supa Dupa” flow, it’s about Sean’s expert vision and his craft. Early on he knew he had something special, and he knew what he wanted to do– there’s an infamous story of how Big Sean first met Kanye while working at Detroit radio station, and preceded to freestyle for him on the spot, evidently winning him over. Sean has always been an easy-going, making it equally easy to connect to his music immediately, doing without any fake deepness, or fakeness altogether, focusing on catchy rhyme schemes and flows, as is the case here.

Given Big Sean’s career thus far, and how he came up, we had to close out this list with a mixtape track (this appeared on Finally Famous 2: UKNOWBIGSEAN), and an important one his catalog no less, as well as a banger that is typical of Sean when it comes to focusing on clever one-offs. There’s just no denying this song as Big Sean an all-time favorite.