In the early 1990s, he moved to Los Angeles, where he would later receive several guest-starring roles and television pilots for networks such as Fox, NBC, and HBO.

[3] While in California, he wrote and starred in several one-person shows, including, Commencement Speech, Life & Other Short Stories, and The Business of Living, the latter directed by Bob Odenkirk.

The main character of The Business of Living, a motivational speaker/success guru named "Jack Freeman", gained a cult following in California and has become increasingly popular throughout the Midwest.

[6] In 2006, he starred in The Friends of Bob & Tom Comedy Central special alongside other comedians such as Bob Zany, Greg Hahn, and Roy Wood, Jr. On April 26, 2008, Comedy Central aired Drew Hastings: Irked and Miffed, Hastings' premiere one-hour television special.

[9][10] On July 12, 2016, Hastings was indicted on four charges, including elections fraud, following a months-long investigation by special prosecutors appointed by a Highland County judge.