Songfacts®:

• When Coolio was asked to contribute a song to the teen comedy Clueless, he already had the gangsta party anthem waiting. A pivotal moment in the film is when Beverly Hills teens Cher (Alicia Silverstone) and her friends go "slumming" at a party in the Valley, where Cher hopes to make a love connection between her socially awkward friend Tai and her wealthy classmate Elton. Tai is dancing along to Coolio's song when she gets knocked unconscious by a flying clog and Elton comes to her rescue.
• The song inspired a catchphrase among Clueless fans, but the film's music supervisor, Karyn Rachtman, wasn't a fan. She thought it sounded too much like Coolio's other party jam, "Fantastic Voyage" - and with good reason. "Rollin' With My Homies" contains the original lyrics to "Fantastic Voyage." Coolio explained to Vulture: "That's what I was going to put out for 'Fantastic Voyage' in the beginning but a guy who worked for Tommy Boy [Records] heard the [original version of] 'Fantastic Voyage' and told me, 'If you change your lyrics a little bit and make it more universal, I think this song could do good.' So I took off the original lyrics and re-wrote the whole song. And the rest is history."
• Just a month after Clueless was released, Coolio landed a massive hit with another soundtrack contribution: "Gangsta's Paradise" from Dangerous Minds.