The series follows a fictionalized version of Ryan Hansen as he attempts to convince his Veronica Mars cast-mates to participate in a spin-off centered around his character, Dick Casablancas.

The idea for the web series originated from Blue Ribbon Content, the digital division of Warner Bros. in response to the ongoing development of the film adaptation of Veronica Mars.

Because he almost did not agree to produce the project, it was almost cancelled; the network brought in several of Thomas's acquaintances to write and direct in order to lighten the creator's workload.

[4] Network executive Mark Pedowitz noted that a premise had not been decided upon at that point and that "[Thomas] talked about potential people being involved, but he didn't commit to anybody.

[7] According to one news outlet, the press release showed the fledgling series' capacity for self-referential humor and numerous celebrity guest appearances.

According to the report, several former Veronica Mars cast members would return as both their characters and themselves, including Kristen Bell, Jason Dohring, Enrico Colantoni, Percy Daggs III, Daran Norris, Francis Capra, Kyle Gallner, and Christopher B. Duncan.

Chris Lowell, Ken Marino, Amanda Noret, and Lisa Thornhill all appeared in the original series but portrayed only themselves or their characters in Play It Again, Dick.

[11] In addition, Ryan Devlin, who had previously acted as rapist Mercer Hayes in the show's third season, portrayed himself and Duncan Kane in the web series.

[12] Slate noted that one notable absence from the cast list was Tina Majorino, who portrayed series regular Cindy "Mac" Mackenzie.

[14] Mike Hale of The New York Times thought that the difference in tone between Veronica Mars and Play It Again, Dick was the most interesting aspect about the web series, writing that it had a "broader, coarser, self-mocking style".

The reviewer stated, "It's an odd little web series, not just because of its mere existence, but because it doesn't exactly have an interesting narrative, nor does it have anything to add to the Veronica Mars universe.