The five best rap songs about Chicago

Thinking about America’s hip-hop heritage, a few cities tend to spring to mind before any others: New York, LA, Atlanta. But Chicago, too, holds an incredibly important place in the culture’s history, even if its reputation isn’t quite as acknowledged.

Chicago is one of the most populous places in America, third only to New York and LA themselves. It is a cultural melting pot, with a deep musical heritage and strong immigrant communities helping to make it what it is. All the ingredients are there, in other words, for a strong hip-hop culture.

Indeed, some great rappers have emerged from Chicago through the years. Most obvious is Kanye West, but other Chicago rappers include Common, Lupe Fiasco, Twista, Chief Keef, Lil Durk, Chance the Rapper, Vic Mensa, King Louie and the late Juice WRLD. There have been lots of them to emerge through the years.

Many of these artists have specifically taken inspiration from their hometown, dropping in references to the city within their songs. Here, then, are five of the best tracks to speak about the Windy City.

5. King Louie – ‘Live and Die in Chicago’

Taking its cue from 2Pac’s 1996 track ‘2Pac’s To Live & Die in LA,’ King Louie decided to pay tribute to his own hometown on 2014’s ‘Live and Die in Chicago.’ His admiration for his city shines through—“Been to Paris, LA, NY to A, to me, they all great / But they not like Chicago”—but he by no means focuses solely on the good stuff. “No murder rate like Chicago,” he also observes on the track.

King Louie has himself fallen victim to Chicago’s violence, having been shot in the head there in 2015. He got lucky and survived, and, within a week, he was appearing on CNN to discuss the city’s problems with violence. “The devil is working overtime in Chicago,” he said, going on to criticise the city’s police force and its gang culture. Louie loves his city, but he’s not blind to its issues.

4. Chief Keef – ‘Chiraq’

Chicago has acquired an unfortunate nickname because of its violent reputation: “Chiraq.” The term is a play on “Iraq,” and it is intended to evoke the violence and chaos that gripped Iraq following the illegal US-led invasion of 2003. The implication of the phrase is that the streets of Chicago, with their high levels of violence, are as dangerous and potentially bloody as those of war-stricken Iraq.

It can hardly be said to be a positive nickname for the city, but Chicago native Chief Keef embraced it with a track he named after it. ‘Chiraq’ is actually a rather wistful song in which Keef pines for a return to his hometown, which he was unable to do because of problems with the law that he was having when he wrote it. For all the city’s faults, Keef’s affection for it is plain to detect.

3. Lupe Fiasco – ‘Go Go Gadget Flow’

The title of Lupe Fiasco’s ‘Go Go Gadget Flow,’ released in 2007, is clearly a reference to the Inspector Gadget franchise, which Lupe has admitted to being a fan of. But the song’s title is actually a reference to a record store in Chicago that he loved when he was younger, and the song more broadly was intended as a tribute to his hometown.

Explaining to The Village Voice in 2007 that he was a “big cartoon fan,” Lupe insisted that the “song really came from the Go Go records in Chicago. In Chicago we say you’re from ‘The Go,’ and so it’s really my anthem for Chicago. Just so Chi-town can have another anthem.”

2. Common – ‘Chi-City’

A braggadocious number in which Common, at times, seems to frame himself almost as a Christlike figure, as opposed to those “whack” rappers that he looks down upon, Chicago also gets plenty of praise in this song from his 2005 album Be. With the track’s producer Kanye West backing him up, Common seems to draw a lot of strength from his hometown.

The track also serves to highlight Chicago as a centre of hip-hop, as important as those other cities that tend to be credited as such. “They ask me where hip-hop is goin’, it’s Chicago-in,” he raps at one point, suggesting that the future of hip-hop lies in the Windy City.

1. Kanye West – ‘Homecoming’

‘Homecoming’ featured on Kanye West’s third album Graduation, released in 2007, and it focused on its maker’s relationship to the place in which he grew up. Ye personifies Chicago as a girl called Wendy—a fairly on-the-nose play on Chicago’s reputation as the “Windy City”—whom he used to be in a relationship with before growing up and abandoning her for fame.

The song evolved from an earlier track that Ye worked on called ‘Home (Windy),’ which actually featured John Legend singing the hook. When it came to redoing the track for Graduation, Ye decided to replace Legend with Coldplay singer Chris Martin. The change of personnel worked, with the track finding huge success in the UK and Europe.