Casting
When the series was first announced, Matthew McConaughey was in negotiations to star, along with returning cast members from Yellowstone. The returning cast members had received offers to appear; however, the contracts would not be finalized until writing on that series was complete. McConaughey's interest in the series arose after he began watching Yellowstone and had a conversation with Sheridan about working on a similar project. Prior to it being repurposed into an independent program, Sheridan decided against including any existing characters early in its development process so that a stand-alone story could be told, once again following a format he explored in Yellowstone's prequels.
Despite this, Luke Grimes, Cole Hauser, Kelly Reilly were at one-time also in negotiations to reprise their roles, after he revealed that decision, because the idea was brought up to him as a way to connect the two shows. Pfeiffer, Kurt Russell, and Patrick J. Adams entered into negotiations around the same time, and McConaughey declined to commit until a teleplay was provided. Hauser and Reilly, described as "quasi-leads" of Yellowstone, both sought significant pay increases to return. Reilly initially requested $1.5 million an episode, which was later negotiated down to $1.2 million. Hauser wished for $1.25 million for each episode, higher than the $700,000 he earned in Yellowstone; Paramount however, was only willing to offer him $850,000 for the first season, rising to $950,000 in season two, with a guarantee for both seasons.
Hauser and Reilly also petitioned to be first-billed among the cast, which was seen as unlikely with the potential of McConaughey and Pfeiffer starring. The two were under pay-or-play filming guarantees from existing contracts for the cancelled sixth season of Yellowstone. Paramount and 101 Studios pitched using the allocated funds from that to cover the raises, but the performers declined holding the opinion that they were already entitled to that money.
Although the two were not negotiating together and could have signed-on independently of each other, representatives for the two remained in contact. In order for them to star, they would have needed to agree to Paramount's and 101 Studios' terms by February 10, 2024. Grimes was reportedly less concerned with receiving a substantial raise. A deal with McConaughey was not reached, and instead, Pfeiffer was the first cast member to be announced in August. Ultimately, no returning characters appeared; however, Grimes, Hauser, and Reilly would go on to star in their own sequels: Grimes in Marshals, a police procedural on CBS, and Hauser and Reilly in Dutton Ranch, a neo-Western on Paramount+. Both programs also featured other former Yellowstone cast members.
Elle Chapman, Adams, Beau Garrett, Amiah Miller, and Matthew Fox were announced as cast members later in August, followed by Ben Schnetzer in October, and Kevin Zegers, Rebecca Spence, Alaina Pollack, and Danielle Vasinova in December. Russell officially joined The Madison as a series regular in September 2025. His delay in joining the show was caused by scheduling conflicts with the Apple TV series Monarch: Legacy of Monsters and resulted in him almost turning the offer down. Russell was filming the second season of that program during the same time that production on the first season of The Madison was occurring. Determined to get him to star, Sheridan and Pfeiffer devised a plan that allowed him to appear in both by approaching Paramount+ executives and requesting the early renewal. The teaser trailer revealed that Will Arnett was also part of the cast and would be featured in a recurring role.
