* indicates required
Okayplayer News

To continue reading

Create a free account or sign in to unlock more free articles.

Already have an account?

By continuing, you agree to the Terms of Service and acknowledge our Privacy Policy

Best Lupe Fiasco Songs
Best Lupe Fiasco Songs
Photo by Aaron J. Thornton/WireImage

The 16 Best Lupe Fiasco Songs

Lupe Fiasco is one of rap music’s most gifted and uncompromising rappers, and these 16 songs — from “Mural” to “King Nas” — are a testament to that.

The lack of universal praise that Chicago rapper Lupe Fiasco receives within rap music is hugely disheartening. The fact that an artist of his caliber, so recognized in the field that he literally teaches Rap Theory and Practice at MIT, doesn't even exist as a footnote on a prominent list of the “50 best rappers of all time” is, at best, confusing. 

In 2006, JAY-Z called the up-and-coming MC a breath of fresh air, and upon dropping his critically acclaimed debut album, Food & Liquor, his promise was all but recognized as he ascended into stardom. However, things got rocky after he released The Cool, primarily due to artistic conflicts between himself and Atlantic Records (which he was signed to).

In a 2019 Twitter thread, he noted that he was "the most blackballed rapper in the history of rap," recalling a conversation with Lyor Cohen, in which a request for a 360 deal in exchange for his masters was met with a cold response of, "If you don't sign [our proposed deal], I can't guarantee we are still gonna promote your albums."

He bluntly added, "From that point forward, I knew my career was over." 

Effectively, his mainstream run was cut short due to his reluctance to play into the industry to the detriment of his vision — and ultimately — his soul. But that was far from the end of his career.

While he may have unplugged from the proverbial matrix, he has been anything but unsuccessful, with his last three studio albums (post-Atlantic Records) earning critical acclaim, and two of those even landing on the Billboard 200 chart: Drogas Light at 28 and Drogas Wave at 60. 

For the seasoned Lupe fans (who love trying to decode the many layers of his music) and new fans alike, Okayplayer is giving the underappreciated genius his flowers. Below are the best 16 gems in his catalog.

16. "Hurt Me Soul"

Throughout his career, Lupe has often found himself championing a thinking man's brand of soulful, conscious rap music. Long before his industry woes with Atlantic, "Hurt Me Soul," off his debut album, saw him parse his mixed feelings about the state and direction of culture. In particular, he wrote about how his morals and personal beliefs differed from the music he grew to love, pointing to the degradation of women and how life had begun to imitate art rather than the other way around.

Given that not much has changed over the years, it sounds just as poignant and timely today as it did in 2006, thanks partly to Needlez's production, ripe with a soul-touching boom-bap aesthetic.

15. "King Nas"

While some thought the song could be about Nas (and a nod to his status and longevity in the game), Lupe made it quite clear that the smooth-as-butter "King Nas" was actually about his nephews, King and Nas. He cleared up the misconception via Reddit, writing: "It's a song I wrote dedicated to and inspired by my two nephews, King & Nas, as they journey into manhood ... I always dedicate songs to my family." 

That still didn't stop some fans from theorizing that there was some homage to Nas, pointing to a few clues including the fact that the song samples the iconic drums from Stanley Clarke's "Slow Dance," famously used by Large Professor for Nas' "It Ain't Hard to Tell" off Illmatic.

14. "Prisoner 1&2" f. Ayesha Jaco

Many of Lu's tracks ("Paris, Tokyo," "King Nas") are written for people in his life, and "Prisoner 1&2" is no different. Carefully crafted for his former manager Charles Patton, aka Chilly Chill, who was convicted in 2007 and is currently serving 44 years in prison for running a drug enterprise, the MoeZ'art-produced song vividly touches on incarceration in America, racial profiling, and the failures of the modern prison system. Split into two parts, one focusing on a prisoner and the other on a guard, it also draws parallels between Patton’s life in prison, and Lupe's metaphorical sentence in the music industry.

13. "The Cool"

Later becoming the basis for The Cool's Michael Young History, Food & Liquor’s "The Cool" is prime Lupe. The song follows a murdered hustler who magically returns to life, digging himself out of his grave and heading back to the block. Of course, the song is so rich in detail that you can almost smell stale alcohol and damp dirt as Lupe raps, "He used his mouth as a shovel to try and hollow it ... working like a reverse archaeologist, except his buried treasure was sunshine."

Then there are bars like, "Pulled himself up out of his own grave and looked at the time on the watch that had stopped, six months after the shots that got him in the box." Chills. 

12. "Paris, Tokyo"

Flipping a sample from Eumir Deodato, Soundtrakk crafted one of the most deliciously soulful records in Lupe's catalog. In some ways, "Paris, Tokyo" emotes a similar sonic vibe to Pharcyde's Dilla-produced "Runnin'." Written for his girlfriend who had to adjust to his heavy touring schedule after the release of his first album, the song is anything but lyrically light, defined by a simple and catchy hook that rounds the track out.

"I'd be gone so much, we'd go for two months at a time without seeing each other," Lupe told Blues & Soul magazine about the song. "It's her song ... just to let her know that, wherever I go, she comes with me—even if it is just mentally or in spirit."

 11. "Ms. Mural"

Drill Music in Zion was undoubtedly one of the better albums of 2022, and this was partially because of “Ms. Mural.” The final installment in a trilogy that started with Tetsuo & Youth’s “Mural” and was followed up by DROGAS WAVE’s "Mural Jr.,” this finale sees him lamenting his past label woes and the creative state of contemporary rap music, using an extended interaction between a painter and his patron that ends with the former burning the latter to death.

Knowing the thought and heart Lupe pours into his music in an era of microwave disposal music, it's not hard to imagine the patron as the embodiment of those incapable (or unwilling) to take the time to understand or appreciate the depth of his art. 

10. "Streets On Fire" f. Matthew Santos

While "Streets On Fire" was initially open to multiple interpretations (the allure of the streets, AIDS, depression, government corruption), the song's description of a fictional plague took on a whole new life 13 years later in 2020, when its lyrics seemed to eerily describe the combination of an ongoing revolution occurring amid a global pandemic. 

Bars like, "No vaccines, remedies, and no corrections, quarantine the dreams and seal off the connections," and "Revolutionaries say it's psychological war, invented by the press, just to have something to report," hit especially hard in the lens of the past few years. Lupe-damus, for real.

9. "Little Death"

This Tetsuo & Youth standout has, in Lupe's own words, "Many pieces running simultaneously." The track plays with the intersection of religion and politics, with the three verses exploring sex, the mistreatment of animals as they're slaughtered, and the justice system, with choruses told through the devil's perspective, attempting to coax the subject into immorality even though it may slowly kill us. 

The instrumental is one of the album's best, but the best way to experience the track is surely this live performance of it on The Tonight Show, with The Roots giving the already live-sounding song even more dimension.

8. "Superstar" f. Matthew Santos

Lupe kicked off his sophomore LP with the Matthew Santos-featured "Superstar," a staple record that explores the addictive and simultaneously soul-crushing reality of fame. The song's first and final verses reference his denial into a club despite his level of notoriety, eventually leading him to hail his chauffeur for a sobering ride home. Although the crux of “Superstar” — his rise and refusal to conform to the industry, and the club serving as an allusion to the celebrity bullshit that comes along with mainstream success — would be a sentiment explored in subsequent work, this track stands out when you consider how much of a departure it was from the Food & Liquor singles that came before it.

Ultimately, the song resonated with fans, earning Lupe his first top 10 Billboard single and helping propel The Cool, his most commercially successful LP to date, to platinum sales.

7. "WAV Files"

DROGAS WAVE, Lupe's seventh studio LP, had a lot of gems. Still, none were as potent as the Lupe and Soundtrakk-produced "WAV Files,” a song spit from the POV of a group of slaves who jumped ships to avoid inevitable slavery. In the process, they became Long Chains, souls who walked back to Africa underwater (although some remained underwater, redirecting the ocean's waves and attacking and sinking slave ships to aid others in escaping their fate). 

The song also finds a way to connect the past with the present, with the idea of the Long Chains becoming "waves" that are contrasted with wav files, best encapsulated in one of the song’s opening lines: “Downloaded by the tidals like JAY-Z."

6. "Dumb It Down" f. GemStones & Graham Burris

If there is one thing Lupe is adamant about, it's not compromising his vision or message for the sake of mainstream accolades. This theme runs through most of his work, and "Dumb It Down" is a theme song for this concept — from its extra-long verses purposely crafted with more depth than the western Pacific Ocean, to its multiple choruses and outros. 

The last bars on the song say it all: "They told me I should come down, cousin, but I flatly refuse, I ain't dumb down nothing!"

5. "Daydreamin'" f. Jill Scott

This 2008 Grammy-winning single (Best Urban/Alternative Performance) exemplifies the upper-echelon level of inventiveness that built Lupe’s early buzz into a fever pitch. Over an obscure Günter Kallmann Choir sample and joined by Jill Scott, Lupe creates an anime-like alter-ego for his project building, describing it as a giant flying robot complete with a plethora of typical hood happenings taking place up and down its metal frame. The second verse satirically looks at everyday rap-isms that still exist so prevalently, providing yet another instance of Lupe’s lyrics being ahead of their time.

4. "Adoration of the Magi" f. Crystal Torres

Amid the jazzy horns, Lupe drops one of his more cleverly-crafted tracks. Even before you get to the raps, there’s already so much going on — from the song’s name referencing artistic depictions of the birth of Jesus Christ to the rapper timing its release on the Epiphany, a religious holiday celebrated when the Magi (the three wise men) first laid eyes on Jesus. 

As for the music, the song's most mind-melting revelation is found in the chorus, as you realize that each line references iconic album covers with babies on them. For example, "Why you ready to die? You just a baby," is a reference to Notorious B.I.G.'s Ready To Die, and "Quit chasing money, never mind, you just a baby," is a reference to Nirvana's legendary Nevermind.

3. "Hip-Hop Saved My Life" f. Nikki Jean

"Hip-Hop Saved My Life" was produced by Lupe's longtime producer Soundtrakk, and was the second single from The Cool. As he explained during an interview with MTV in 2008, he aimed to create another version of the track "Kick Push" that instead focused on a hungry Houston, Texas, rapper trying to make it in the industry. The song was dedicated to Bun B, but Slim Thug's career inspired it.

2. "Mural"

In this first installment of his "Mural" trilogy, he presents a nine-minute master class in crafting intelligent, lyrically elite bars stripped of mainstream conventions. It was a clear standout on Tetsuo & Youth, so much so that even UK-based rap music statistician Hip Hop By The Numbers made note of how intricate the track was, encompassing 153 bars, 1,373 words, and a mind-boggling 785 unique words.

1. "Kick Push"

His debut single from Food & Liquor, "Kick, Push," remains an absolute classic. While it displays the wit and lyrical inventiveness Lupe would later bolster to incredibly high heights, it remains straightforward in an endearing way. Borrowing its lush cinematic sound from an ‘80s Celeste Legaspi record, the Soundtrakk-produced song's three verses explore the coming of age of a young boy — from the moment he falls in love with skateboarding to meeting his girlfriend and finding a crew of like-minded rollers. 

A monument to obscure sampling — it’s arguably one of rap music’s best beats — “Kick, Push” is a song that seems impervious to age, still just as great as it was when it first dropped.

Riley is a Toronto-based rap music writer and vinyl head. You can follow him on Instagram at @rileywallace.