Creative Loafing began as a family-owned business in 1972 by Deborah and Chick Eason, expanding to other cities in the Southern United States in the late 1980s and 1990s.

In 2007 it doubled its circulation with the purchase of the Chicago Reader and Washington City Paper; the $40 million debt it incurred, along with an economic recession, forced the company into bankruptcy one year later.

Investigative report and CL Editor CB Hackworth's piece on racial segregation brought Oprah Winfrey to Forsyth County to confront overt racism in 1987.

Other newspapers the company published over its 40-year history included: Deborah Eason, a photographer for Delta Air Lines, and Elton "Chick" Eason, a math professor at Georgia State University, founded Creative Loafing Atlanta in 1972 after the couple attended a 25-attendee Georgia State University lecture by a visiting Russian scholar.

This, and other poorly attended events, convinced them to start Creative Loafing Atlanta to inform the public about all of the city's cultural happenings—festivals, concerts, Wicca meetings.

[1] Creative Loafing was not the first alternative weekly Atlanta had seen, but over the years, its size and ambitions crowded out competitors—The Great Speckled Bird; Poets, Artists & Madmen; The Sunday Paper.

[1] After a decade and a half in Atlanta, the Easons established new Creative Loafing weeklies in March 1987 in Charlotte, North Carolina,[14] and in 1988 in Tampa, Florida.

[9] By July 2007, Creative Loafing became a mini-empire with four papers in three states and purchased two heralded alt-weeklies—the Chicago Reader and the Washington City Paper—and The Straight Dope, a longtime Reader-syndicated column by Cecil Adams.

[15] Two years later, in September 2000, he and his two sisters led a group of investors to purchase a controlling interest in the entire Creative Loafing chain, and subsequently brought the Planet papers into the fold.

[8] To help finance the 2000 deal transferring ownership to Ben Eason's group, media conglomerate Cox Enterprises purchased a 25% minority share of the company for approximately US$5 million.

After the Journal-Constitution in April 2003 quietly launched its own free entertainment weekly named Access Atlanta, in direct competition with Creative Loafing, the Easons and Creative Loafing board members voted to censure the two Cox executives for unethical conduct, and by June 2004 both companies agreed to allow the chain to repurchase its shares from Cox.

[3] Two months later, on July 3, Creative Loafing Atlanta and the Washington City Paper were sold to SouthComm Communications for an undisclosed sum, and CL Inc. ceased to exist.