The members of The Cool Kids met in 2005 when Reed found a beat on MySpace that Ingersoll had produced. The two met to discuss terms of the beat’s sale, and eventually ended up recording for two hours. They were inspired by golden age hip hop and artists like Eric B. & Rakim. Ingersoll began promoting the new duo’s material, and it was eventually booked by Josh Young of Flosstradamus for a DJ performance. At this performance (in a venue called Town Hall Pub), the duo met the DJ Diplo who offered to release a mixtape of their unreleased tracks titled Totally Flossed Out on his label Mad Decent, though it was eventually released on C.A.K.E. Recordings. They also received an offer from the DJ A-Trak to sign to his Fool’s Gold label, which they did, but only for one single. Of their time with Fool’s Gold, the Cool Kids felt they weren’t getting enough attention: “When your boss is on tour with Kanye West, it’s easy to have timelines missed,” said Chuck in an interview.
All of their material had been released solely on the band’s MySpace page—their recording contract came after performances at the CMJ Music Festival and Pitchfork Media Music Festival, on July 15, 2007. Eventually, The Cool Kids signed to Chocolate Industries, another independent label. The group has revealed on its MySpace page that The Cool Kids’ debut album, When Fish Ride Bicycles, will be released in 2008, though as of 2010 it has not been released. Ingersoll has been the producer for tracks released thus far, but both work in rapping and production. The duo uses music software program Reason from Propellerhead Software to produce their music.
They have been on tour, opening for M.I.A. and they will be also joining the bill of the 2008 Rock the Bells hip hop festival on select dates. The group toured across Australia in February 2008 and also appeared at the Laneway Festival. The group also appeared at SUNY Purchase’s Culture Shock event in April 2009. One of the duo’s singles, “Black Mags”, was featured in a late 2007 Rhapsody TV commercial, along with Sara Bareilles. In the same year, the group collaborated with Lil Wayne and DJ Benzi through the Internet on a track entitled “Gettin’ It”, which will reportedly appear on the DJ’s future album Get Right.
The Cool Kids have been featured in the video games NBA Live 08 and MLB 2K8 with the song “88″, in Need for Speed Nitro, with The Bloody Beetroots in the song Awesome, and in the episode “The First Cut Is the Deepest” from HBO’s TV series Entourage with the song “Mikey Rocks”. They were listed in Rolling Stone’s Ten Artists to Watch in 2008. According to Rolling Stone, “since “Black Mags” debuted, the Cool Kids have gone from an underground sensation in their native Chicago to the hottest ticket at New York’s CMJ festival.”
The duo has been endorsed by Mountain Dew for their single, “Delivery Man”, to which commercials and the music video have aired on MTV2. The group’s song “Bassment Party” was featured in the September 21, 2008 episode of the HBO hit comedy Entourage. They also recorded an original track, “2K Pennies,” for the soundtrack of NBA 2K9However, The Cool Kids have said in an interview that their success has been gradual. They will also be headlining the “NBA 2K Bounce Tour” along with Q-Tip. The Cool Kids also performed at the 2009 Voodoo Experience in New Orleans, Louisiana. Producer Don Cannon said in an interview with XXL, that he will be working with The Cool Kids for their new album. The group’s second official mixtape, Gone Fishing was released on May 5, 2009. They are currently working on their debut album, When Fish Ride Bicycles, which was released July 12, 2011.
Their song “A Little Bit Cooler” was used in a “Most Valuable Puppets” commercial from Nike with LeBron James and Kobe Bryant entitled “Mrs. Lewis”. A new mixtape called Tacklebox came out on May 31, 2010. Chuck Inglish worked with Chip tha Ripper and produced his debut album Gift Raps in its entirety. The group claims they haven’t put out an album because of having issues with their former label Chocolate Industries for the past three years, but according to the group these issues are now settled and they are working on putting out When Fish Ride Bicycles.
Chuck Inglish and Mikey Rocks recently teamed up with Gary, Indiana’s Freddie Gibbs and Cleveland’s Chip tha Ripper to form the “super group” P.O.C. (Pulled Over by the Cops). Sir Michael Rocks has released a solo project titled The Rocks Report. When Fish Ride Bicycles was finally released on July 12, 2011. Featuring production by The Neptunes and also featuring Bun B, Chip Tha Ripper, Ghostface Killa, among other artists. The group plans a follow up album titled “Shark Week”.