Roberts returned to the United States in 1986. He found a job at Origin Systems, where he created Times of Lore, published in 1988. The game's interface had a strong influence on other Origin products such as the popular Ultima series. A similar game system was used in Roberts's next release for Origin, Bad Blood (1990).

Wing Commander was published later in 1990 and was highly acclaimed. Wing Commander (and the franchise it spawned) soon became Origin's most successful product. Roberts wasn't as heavily involved in the sequel Wing Commander II, which he only produced. He instead concentrated on Strike Commander. First shown to the public at Summer CES 1991, the project suffered from numerous delays and was not released until 1993. He returned to Wing Commander soon after, devising the original concept for the spin-off Wing Commander: Privateer (which his brother, Erin Roberts, produced) and being more deeply involved in Wing Commander III and Wing Commander IV. For these sequels, Roberts directed the live-action cinematic scenes. Roberts's major role in developing the Wing Commander games led Next Generation to name him one of their "75 Most Important People in the Games Industry of 1995".

Roberts left Origin in 1996 and founded Digital Anvil along with EA PC national sales manager Marten Gerald Davies, Tony Zurovec, Eric Peterson, John Miles & his brother Erin Roberts. The fledgling studio set up shop in Austin and for several years worked quietly, inking a publishing deal with Microsoft in 1997.

Roberts had stated that he desired to produce films as well as games with Digital Anvil. The 1999 feature film release of Wing Commander directed by Roberts himself, starring Freddie Prinze Jr. and featuring visual effects from Digital Anvil failed to attract either critical praise or financial success.

Digital Anvil's first finished game was Starlancer, released to a generally favorable critical reception in 2000. Developed jointly between Warthog and Digital Anvil, the game was produced by the Roberts brothers, and Eric Peterson. The company was acquired by Microsoft soon after, who sold two of Digital Anvil's projects Conquest Frontier Wars led by Eric Peterson, and Loose Cannon led by Tony Zurovec to Ubisoft. Roberts left the company after the acquisition, abandoning the Director position of his ambitious project Freelancer, although he remained with the game in a consulting role for a while. The game was commonly regarded as vaporware due to its promised release date of 2001 however it was eventually released in 2003 with a markedly different feature set than the initial plans. It was received very favorably with a Metacritic score of 85%.

After leaving Digital Anvil, Roberts founded Point of No Return Entertainment, planning to produce films, television and games. However, no projects materialized from Point of No Return. Roberts founded Ascendant Pictures in 2002 and served as a Producer for a number of Hollywood productions including Edison (film), Timber Falls, Outlander (film), Who's Your Caddy?, The Big White, Ask the Dust (film), Lucky Number Slevin and Lord of War. In 2005 actor Kevin Costner sued Ascendant Pictures for breach of contract on an unreleased film. The company later was acquired by Bigfoot Entertainment in 2010.

In 2011, Chris Roberts founded Cloud Imperium Games, together with his Business partner and long-time international media attorney Ortwin Freyermuth, to work on a new game. In October, 2012, Cloud Imperium Games launched a crowdfunding campaign on their web-page to produce a space sim game, Star Citizen, later add a Kickstarter campaign in conjunction. By November, 2012, they had earned $6,238,563, surpassing all stretch goals set for the campaigns, and breaking video game industry crowdfunding records. Chris Roberts had stated that if at least $23 million could be raised over the course of the crowdfunding campaign, no outside investors' or developers' funding would be required. This goal was reached October 18, 2013.