Speculating the ‘Very Special Suprise Guest’ for AAHH! Fest


Photo by Dan Garcia/The Early Registration
Photo by Dan Garcia/The Early Registration

Later this month, Chicago’s Union Park is hosting Common’s AAHH! Fest. As announced last week, legendary comedian Dave Chappelle will be hosting this years event, which features a number of Chicago artists and one “very special surprise guest”. Time to speculate who that may be!

The festival will feature a number of great acts, including Common, Lupe Fiasco, De La Soul, Jay Electronica, Lil Herb and more, but the billed “very special surprise guest” (not just “surprise guest”) is especially intriguing.

This guest likely will have two qualities, based off obvious context clues. (1) They likely are from Chicago, as the majority of the line-up is from Chicago and the festival of course is in Chicago. And (2) the act should be big enough that it warrants being billed as a ‘very special surprise guest’. We would love to see Chicago’s Vic Mensa perform at the fest for example, but he would not get billing over Lupe Fiasco.

Two of our reasoned guesses shared a stage in Chicago just a month ago, Chance the Rapper and R. Kelly. Chance the Rapper is of course one of Chicago’s biggest names right now and promotes a lot of the same anti-violence messages that Common has been promoting for his city. Also, while his fall tour starts soon, Chance does not have any scheduled tour dates on September 21st (the day of AAHH! Fest), and kicks off his own tour on the 26th. It is hard to find someone in Chicago that wouldn’t love to see Chance, for probably their 10th time, and he is one of the kings of music festivals this year. Technically there is a strong possibility Chance isn’t supposed to perform in Chicago up to three months after Lollapalooza, due to Lollapalooza’s contract clauses (which although not public are rumored to prevent artists at Lollapaooza from playing shows within 300 miles of Chicago up to six months before and up to three months after Lollapalooza). However, maybe there is a legal loophole if Chance is billed as a very special guest, or maybe he just doesn’t care (if he is the special surprise guest of course).

R. Kelly is also a realistic option, as he was just a surprise guest for Chance the Rapper’s Lollapalooza performance. R. Kelly still lives in the city, has no scheduled shows for that day, and who wouldn’t love to see Robert make an appearance? This may be unlikely though because he was literally just a special guest at a Chicago festival just a month ago, but Lollapalooza’s contract clauses wouldn’t prohibit him from performing since they didn’t write him any checks this year. A second surprise festival performance though is a little redundant perhaps. Another legendary Chicago rapper that could perform at the festival is Twista. Twista is also no stranger to surprise performances in his city, as he was Chance the Rapper’s surprise guest at Lollapalooza in 2013. Although while he is certainly an option, he maybe isn’t big enough to have billing over Lupe Fiasco and De La Soul.

Another Chicago rapper who is big right now, and would likely warrant the titled of “special surprise guest” is Sosa himself, Chief Keef. This wouldn’t be the biggest surprise in the world since Common’s latest album Nobody’s Smiling certainly centers around the current stage of Chicago and touches base on the Chi-raq drill scene. Also Lil Herb, another Chicago drill rapper, is billed on the line-up, so a Sosa performance would not be out of context. Unfortunately however for those who want to see Chief Keef perform, he has a couple warrants out for his arrest in the state, so he may want to lay low. Maybe that’s why its a secret though?

Now, to our best and most wishful guess, Chicago’s own Kanye West. In this case, there are a number of strong reasons why it could and why it could not be Kanye. To start with the reasons why it likely will not be Kanye, for one, is he too big for this appearance? Why not just bill Kanye on the line-up, jack up ticket prices, and still sell substantially more? Also, Kanye is currently finishing up his 7th studio album and has a number of a performances in Australia this month, although none on September 21st. Finally, unlike some of the others, Kanye does not spend a huge amount of time in Chicago these days. Don’t forget too the man has a family now and is immensely busy.

However, there are many reasons we are hopeful. Of course, Kanye has a long relationship with Common. The man produced some of Common’s best records and until just recently Common was on Kanye’s G.O.O.D Music. Also Kanye has a long friendship with AAHH! Fest’s host, legendary comedian Dave Chappelle. Lupe, De La Soul and Rhymfest are not strangers to Kanye either. Of course too, Kanye is from Chicago and has been on a festival kick all summer. Also, while Kanye is certainly a huge name and making that public would boost tickets immensely, he has been a surprise guest for festivals before. Just last year he was a surprise guest at Drake’s OVO Fest. Perhaps the strongest piece of evidence though is that Donda House Inc., which provides premium art access to Chicago youthis in partnership with the festival. Of course, Donda House is founded by Kanye, named after his late mother, Donda West.

It may just be wishful thinking but our guess has to be Kanye. Whoever it may be though, AAHH! Fest certainly will be a can’t miss event for all.

Visit AAHHFest.com for tickets and more information.


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