Listen to Sean Connery.

Never bring a knife to a gun fight.

Be fully prepared with your pop facts before stepping up to this colorful, controversial cultural critic and humorist based out of Chicago. Kyra Kyles — currently a writer and culture commentator for hire– will hit you with an aerial intellectual attack, using the TV, radio, print and digital skills she honed long before being a multimedia journalist was en vogue.

Through her column and blog, The Kyles Files, the native South Sider has tackled tough issues of racism, sexism, homophobia and media elitism, as seen through the prism of pop culture.

Kyra — winner of a coveted Jones Beck editorial award from the Chicago Tribune– also holds it down as an on-air contributor for WGN-TV, each week delivering an on-target analysis of the biggest issues in celebrity culture.

An innovator in the digital space, Kyra developed and launched an original talent contest, the Kyles Files track-off, to place the spotlight on Chicago rappers, rockers and singers.

A social media expert with a rapidly expanding and enthusiastic following on Twitter, Facebook and Google +, Kyra is a regular speaker for the Community Media Workshop, Columbia College of Chicago, as well as Northwestern University’s Integrated Marketing and Medill programs.

In addition to RedEye, Kyra’s content has appeared in the Chicago Sun-Times, the Chicago Tribune, Rap Sheet, and She is a regularly featured pundit on WBEZ-FM, WVON-AM, WFLD-TV, and CLTV to name a few.

A longtime proponent of diversity in media, Kyra is the twice-elected president of the National Association of Black Journalists-Chicago chapter, and has served on the award-winning organization’s board for five years. Among her accomplishments for NABJ-Chicago, she revamped its digital strategy, launched a minute-to-win-it power networking series involving local entrepreneurs, and pioneered the NABJ-Chicago mentorship program, one of its most popular member benefits.