The latter first appeared on Posner's October 2009 mixtape One Foot Out the Door; its production is largely identical to the final song, although this version's structural arrangement is different, lacking any verses.

[4] Speaking in August 2010 to noted British urban writer Pete Lewis – Assistant Editor of Blues & Soul – Posner described the background to the song: "A lotta people don’t know I recorded that song while I was still a student, and that I recorded it in my dorm-room on an extremely cheap microphone!

[6] After a short ride in an elevator, Posner enters a hotel suite, where he finds a party in freeze frame.

Throughout the course of the video, Posner tries on different styles of sunglasses including Oakley Razorblades, Holbrooks, Jupiters, Frogskins, and 3D glasses.

[8] Posner appeared on TBS's Lopez Tonight on May 31, 2010, with a performance of "Cooler than Me" (Gigamesh Remix), as well as America's Got Talent on July 28, 2010.

It was also covered in the 2011 season of the Australian version of The X Factor by boy band Young Men Society, who made it to the top eight before being eliminated.

The song is featured on the re-mastered edition of Grand Theft Auto V for PlayStation 4, PC and Xbox One versions released on November 18, 2014.