The company was founded in 1965 by Ralph Tyler, when it purchased KEBC radio in Oklahoma City; Tyler owned the station for 14 years until 1986.^[4] Tyler re-entered the radio business in 1994 with the purchase of a station in Ada.^[4] Tyler Media entered the television industry in 2004 after it purchased Oklahoma City television station KQOK (channel 30). After the sale, Tyler Media converted the station into a Telemundo affiliate and recalled the station to KTUZ-TV after its new radio sister.

On April 16, 2009, Tyler purchased five affiliates of the Spanish-language network Univisión at an auction held by Equity Media Holdings, which was liquidating its assets that year due to bankruptcy.^[5] After the sale was approved by the FCC, this created a duopoly with KTUZ-TV.^[6] Equity had owned both stations at some point, KTUZ-TV was owned by Equity from sign-on until 2004 when Equity traded channel 30 to Tyler Media in exchange for KUOK.

On July 15, 2012, Tyler Media entered into an agreement with Renda Broadcasting to purchase that company's Oklahoma City radio cluster (KMGL, KOMA, KRXO and KOKC) for $40 million. In accordance to limits imposed by the Federal Communications Commission on the number of radio stations a single broadcasting entity can own in a single market, Tyler sold KTLR-AM/FM and KKNG to WPA Radio for $1.6 million.^[7][8]

In early 2017, Tyler Media launched its newest marketing extension called, Tyler Media Digital.