The duo was introduced by former band member Zachary Sewall in late 2008 while the two were studying at Drexel University,[3] in Beresin's hometown of Philadelphia.

Anamege's sound is based on the fusion of hip hop and alternative using samples from artists such as Ellie Goulding, Radiohead, Sufjan Stevens, Passion Pit, MGMT, Matt and Kim and Yelle.

Pretty Much Amazing continued to occasionally release new songs from the duo and in November 2009 debuted the group's first free mixtape entitled The Swelly Express.

The duo have had appearances in several video games, such as in the sports game NBA 2K12 with their song "Here We Go" from their EP The Preview, featuring rapper Q-Tip of hip hop group A Tribe Called Quest, as well as in Madden NFL 12 with their song "Mind Your Manners" featuring Swedish electropop duo Icona Pop.

Their single "Opposite of Adults" was included in the racing game Need for Speed: Hot Pursuit, in addition to being chosen as the goal song for Team North America in the 2016 World Cup of Hockey[6] as well.

The mixtape quickly gained a music following from its online hit "Opposite of Adults" (which includes a sample from MGMT's song "Kids").

The mixtape was praised by fans for the production style, including samples from Passion Pit ("Truth"), Tinie Tempah and Pogo ("Expialidocious").

The songs "Opposite of Adults", "Truth", "Fresh Like Us", "All Things Go" (including a sample from Sufjan Steven's "Chicago"), and "Dream Chasin'" have been re-released for download via the iTunes Store since the release of the mixtape.

It consists of 15 tracks featuring fellow rappers including Trae tha Truth, Casey Veggies and Mac Miller as well as singer eLDee the Don and electronic music duo The Knocks.

A series of "Mind Your Manners" remixes, including one with Travie McCoy, were released later in 2012 in the form of two EPs (one featuring a previously unreleased song titled "Twisted").

However, Chiddy Bang did not release any music in the years 2013-2016 until returning with a trio of singles in 2017: "Been a While", "Same Old Thing" (produced by Russ), and "Came a Long Way" (featuring BeWill).

On April 29, 2011, after rapping for 9 hours, 18 minutes, and 22 seconds at MTV's inaugural O Music Awards in Las Vegas, Chidera "Chiddy" Anamege earned himself a place in the Guinness Book of World Records for Longest Freestyle and Longest Continuous Rap, a title previously held by Canadian rapper D. O., in August 2003 at 8 hours and 45 minutes and 23 seconds.