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ESSENTIALS: Hand Wale His Flowers After Listening To This Playlist

  • October 17, 2025
  • Ryan Shepard
RALEIGH, NORTH CAROLINA – APRIL 6: Wale performs onstage during the 2025 Dreamville Music Festival at Dorothea Dix Park on April 6, 2025 in Raleigh, North Carolina. (Photo by Prince Williams/WireImage)

No one person or entity will ever be bigger than the culture of Hip-Hop. However, every era, chapter, and period within it has figures, trends, movements, and groups that are essential to telling the larger story of what Hip-Hop is, can be, and will eventually become. For the better part of the last 15 years and change, Wale has been one of these figures for the modern era. Sure, he’s often overlooked in popular media when framing the “Big 3” discussion that’s consumed social media conversations over the last two years or so. But it’s impossible to look past his contributions to sneaker culture within Hip-Hop, classic features on songs like “No Hands,” or how he’s waved the flag for the nation’s capital when so many look past the city’s rich Hip-Hop and R&B scene — Ari Lennox, Rico Nasty, Oddisee, Fat Trel, Alex Vaughn, Shy Glizzy, and the list goes on. In fact, it’s incredibly long when it’s expanded to the entire DMV.

More than a decade into the game, Wale’s resumé speaks for itself, but that doesn’t mean the hunger is gone. In reality, it’s probably grown stronger. Over the last year, Wale’s been rapping like he’s in a contract year. Freestyles over “CRG,” “Yukon,” and the Don Cannon-produced “James” sound like the work of someone who’s put in 10,000 hours and then some. Simultaneously, he’s expanded his portfolio outside of the booth, collaborating with Nike on the Cherry Blossom Foamposite One and executive producing a series about the life of Wayne “Silk” Perry. With everything moving in the right direction, Wale has unveiled the release date for his eighth studio album, Everything Is A Lot. As he prepares for its mid-November release and accompanying Gifted Week, Def Pen unveils its latest addition to the growing ESSENTIAL playlist series.

“My Sweetie”

Year: 2009

Album: Attention Deficit

Years before many of America’s biggest Hip-Hop, Pop, and R&B acts were infusing elements of Afrobeats and neighboring genres, Wale was running to the recording studio and finding ways to showcase his Nigerian heritage in his music. As he says in the song’s opening seconds, the song is intended to sound and more importantly, feel like the music he heard when his Mom used to take him “to the African parties” in and around Washington, D.C. While it didn’t reach the commercial heights of a “Chillin” or a “Nike Boots,” “My Sweetie” is a staple of his debut album, Attention Deficit.

“Bait”

Year: 2011

Album: The Eleven One Eleven Theory

It is impossible to discuss the music and culture of the nation’s capital without mentioning Go-go music. Like House Music is to Chicago and Club Music is to Baltimore, Go-go is not simply a percussion-heavy, funky genre of music; it’s a culture. Furthermore, it’s a type of music and culture that is woven into the DNA of Wale’s discography. From songs like “Bait” to the more recent “Jump In” on Folarin II, Wale has never shied away from infusing pieces of his hometown in the popular music space. On the 2011 mixtape The Eleven One Eleven Theory, Wale is at his best as he combines Go-go with trap while referencing the Goodman League and Towson as he uses DC slang in bar after bar. Not to mention, the legendary band, TCB, leaves their distinct style in every note of the song. “Bait” is as much of a club banger as it is an ode to the DMV and its rich music scene.

“Dearly Beloved”

Year: 2021

Album: Folarin II

Want to see a hardcore Wale fan crash out in real time? Ask them about “Dearly Beloved” featuring Jamie Foxx. Released in 2021 on Folarin II, the Maneesh, RZN, and Wale co-produced track finds the DMV native rapping as if he’s leaving a voicemail for an ex-lover hours before her wedding. The track’s deeply personal nature paired with the soulful Jamie Foxx sample make for a song that will stick in your mind long after it stops playing. However, the song, which is less than two minutes, will stop playing fairly quickly. For years, Wale has jokingly gone back and forth with fans on social media about the song’s short runtime. While it appears that fans will never get a full-length version of the track, they’ll get a full-length album instead as he prepares to release his eighth studio album later this fall. In the meantime, work your way through some of Wale’s greatest hits, B-sides, and favorites below as part of our ESSENTIALS playlist series.

Related Topics
  • Wale
Ryan Shepard

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