Founded in 1988, the chain was the largest direct competitor to Blockbuster Video until it was acquired by Movie Gallery in 2005.

In 1985, Wattles borrowed money so he could open a 500 square-foot video rental store with 300 films, located in downtown Portland, Oregon.

Blockbuster alleged that the employees knew some of the company's trade secrets, which could be used to aid Hollywood Entertainment.

In May 1995, a judge ruled in favor of Hollywood Entertainment, stating that Blockbuster had failed to demonstrate irreparable harm as a result of the hiring.

[10] In 1996, Hollywood decided to establish three regional offices, with one each in the Chicago, Houston, and San Francisco Bay Areas.

In response, Hollywood Video agreed to a buyout on January 10, 2005, by Movie Gallery, a smaller competitor.

The site used an automated "social scoring algorithm" to link to articles on the web pertaining to movies and other entertainment media content.

In 1996, Poorman-Douglas Corp agreed to occupy all of the space in the Beaverton building, relieving Hollywood of extra rent payments.

[16] After Hollywood decided to leave Beaverton, it signed a long-term lease for a 166,000 square feet (15,400 m2) building in Wilsonville, Oregon.

Robert Goldfield of the Portland Business Journal said that Hollywood Video "barely" took occupancy of the structure; then Mark Wattles, the chief executive, decided to move the offices and the Hollywood Video headquarters to the former Smith's Home Furnishings headquarters in Wilsonville.

[5] The 173,000 square feet (16,100 m2) headquarters facility was no longer occupied by October 1998; as of that month the space was for lease.