The five biggest Chicago rap songs of all time
The Chicago rap scene is too big and has too much history to capture in a list. And to simply state the “greatest” songs would be too daunting of a task.
So this list will cover Chicago’s biggest rap songs – the ones that changed the game, put artists on the map, and cemented Chicago as much more than the Second City when it comes to rap.
Let’s start by saying that Chicago has many legendary rappers, and just because an artist’s song isn’t in the top five doesn’t mean they aren’t a key building block of the Chicago scene. If there was room for Lupe Fiasco, Mick Jenkins, Noname, Saba, Polo G, Lil Durk, King Von, Saba, Crucial Conflict, Twista, Vic Mensa, and so many more, the list would be much more complete.
But out of all of these greats, we’ll focus on just five songs that cover the key eras of Chicago rap.
The five biggest Chicago rap songs of all time:
‘I Used to Love H.E.R.’ – Common (1994)
This was the song that arguably put one of Chicago’s most iconic rappers on the map. It was the lead single off Common’s second studio album, Resurrection. Now, the song has come to be a defining example of Common’s laid-back, poetically woven lyrical style.
“I Used to Love H.E.R.” also gets a spot on the list for being produced by legendary Chicago DJ, No I.D. Talking about Chicago rap without mentioning No I.D. would be like talking about Detroit rap without mentioning J Dilla.
There are plenty of great Common songs out there, but this one holds it down for Chicago in the 1990s.
‘Homecoming’ – Kanye West (2007)
Choosing the biggest song from Kanye’s discography is a nearly impossible task, but if you’re talking about Kanye’s connection to Chicago, it’s hard to pass this one up. This classic came from Kanye’s third album, Graduation, and features Coldplay singer, Chris Martin, on the chorus.
Of course, the entire song is an ode to Chicago, but it has an even deeper connection to Chicago rap than just that. Back in the demo phase of Kanye’s first album, College Dropout, he had a song called “Home (Windy)”, with John Legend providing vocals.
The song was styled after none other than Common’s ‘I Used to Love H.E.R.’. But the demo was left on the cutting room floor. That was, until it was later reworked and retitled ‘Homecoming’. But no matter which version you listen to, you’ll hear the same Chicago-centric lyrics from Ye.
‘I Don’t Like’ – Chief Keef (2012)
Chicago’s drill scene developed too organically to cite a single origin, but if you were to point to one of its first and most popular examples, this would be it. While a song like ‘Love Sosa’ might have more listens on Spotify, ‘I Don’t Like’ takes this spot for being Chief Keef’s first to blow up.
The song was featured on his 2012 mixtape, Back from the Dead, and went on to chart on the Billboard 100. That alone is remarkable – a single from a mixtape charting among the top 100 songs on the radio. But from there, the song would be reissued on Chief Keef’s debut album, Finally Rich, and eventually remixed by Kanye West.
And while the wildfire of popularity from Chief Keef’s debut is one thing, the most incredible part is remembering that Chief Keef was 16 when he released ‘I Don’t Like’.
‘No Problem’ – Chance the Rapper (2016)
If one song stands out as the Chance anthem, the one you can almost always guarantee he’ll play when he makes a surprise appearance at Lollapalooza, it’s this one.
In the 2010s, Chance the Rapper was Chicago’s star. His mixtape, Acid Rap, had put him on the map in 2013. With Coloring Book, he fully established himself as a major player in hip-hop, including features from Kanye West to Justin Bieber.
‘No Problem’ was no different, featuring Lil Wayne and 2 Chainz. The song went on to win the 2017 Grammy for Best Rap Performance.
‘Lucid Dreams’ – Juice Wrld (2018)
If you want to talk about the “biggest” songs to come out of the Chicago rap scene, it can’t get much bigger than ‘Lucid Dreams’.
The song was initially released on Juice Wrld’s Soundcloud in 2017, and then was re-released as an official single in 2018. It went on to peak at number two on the Billboard 100, and has over 2.9billion streams on Spotify, making it one of the most-streamed songs on the platform.
Especially in the wake of Juice Wrld’s early passing in 2019 at the age of 21, this blend of emo and hip-hop hits right in the heart. And while he’s often remembered for that melodic style, the dude could also rap like crazy, as anyone who’s seen his one-hour freestyle videos on YouTube would attest.