Since 2000
Brolin played General Ralph Landry, outgoing director of the Office of National Drug Control Policy in Steven Soderbergh's Oscar-winning Traffic (2000); as Jack Barnes in Steven Spielberg's Catch Me If You Can (2002); a minor role in the 2003 comedy A Guy Thing; as philandering husband Robert Hatch in the 2006 comedy The Alibi (released in the UK as Lies and Alibis); as Jack Jennings in the 2007 film The American Standards; as TV network anchor Frank Harris in Richard Shepard's The Hunting Party (2007); and starred alongside Emma Thompson and Dustin Hoffman in Joel Hopkins' 2008 film Last Chance Harvey (2008).
In 2002, Brolin played Governor Robert Ritchie of Florida, the Republican nominee running against President Jed Bartlet, on the TV series The West Wing.
In late 2003, Brolin portrayed Ronald Reagan in the television film The Reagans. The film was originally meant to air on CBS, but after creative differences, scripts controversies, and rising costs, CBS passed on the film, and it aired on cable channel Showtime, also owned by Viacom. The role earned Brolin his fifth Emmy Award nomination, as well as his fifth Golden Globe nomination.
In 2005, Brolin guest starred as casino owner Daniel Thorn in the TV series Monk. In 2006, Brolin appeared in the A&E Network film Wedding Wars, playing an anti-gay marriage governor. In 2008, Brolin guest starred on Law & Order: SVU as astronaut Col. Dick Finley. The same year, Brolin also starred in the lead role in the Sci-Fi Channel film Lost City Raiders.
Brolin appeared in the 2009 comedy film The Goods: Live Hard, Sell Hard. He also appeared in a 2009 episode of Psych, titled "High Noon-ish", where Brolin played the sheriff of a tourist-attracting "Wild West" town. The episode was in part a parody of the 1973 film Westworld, in which he had starred.
Brolin has played Richard Castle's mysterious father in two episodes of ABC's Castle, (2013-2014). He appeared as William Winger, Jeff Winger's estranged father, in the NBC sitcom Community.
From 2015 until 2019, Brolin played the role of John, the family patriarch, in the CBS comedy Life in Pieces.
In his first role in an animated film, Brolin portrayed Emperor Zurg in the 2022 Toy Story spin-off film Lightyear.