In 1995, he became engaged to Juliette Hohnen, then the Los Angeles bureau chief for MTV News, and they married on July 29 that year at Highclere Castle in Berkshire, England. Hohnen filed for divorce on February 6, 2013, after 17 years of marriage. The couple have two sons.

He appeared in four Stephen King adaptations: Desperation (2006), “You Know They Got a Hell of a Band” from the Nightmares & Dreamscapes (2006) mini-series, ”Revelations of Becka Paulson” from the “Outer Limits” revival series, and in the television mini-series version of Stephen King’s The Shining (1997), playing the murderous writer Jack Torrance. He also narrated the audiobook version of King’s novel It. In 1998, he played the voice of wisecracking Alsatian Charlie B. Barkin in An All Dogs Christmas Carol, a role he earlier played in 1996 in All Dogs Go to Heaven: The Series.

Weber first appeared on Broadway in Tom Stoppard’s The Real Thing and in 2001-2002 took over for Matthew Broderick as Leo Bloom in the Broadway production of The Producers. In 2005, he appeared alongside Kevin Spacey in London at the Old Vic’s production of National Anthems. Weber also wrote and produced 2003’s Clubland, a Showtime movie in which he and Alan Alda played father and son talent agents in 1950s New York City (for which Alda was nominated for an Emmy).

In 2007, he rejoined former Wings co-star Tony Shalhoub in a guest role on Monk. The same year, Weber played the role of network boss Jack Rudolph in the NBC series Studio 60 on the Sunset Strip. In 2008, Weber starred in Alliance Group Entertainment’s feature film Farm House, where he played Samael, a mysterious vineyard owner. Weber also guest starred on the drama series Brothers and Sisters as Graham Finch, a business specialist. He also guest-starred on Psych as Jack Spencer, Shawn Spencer’s uncle and Henry Spencer’s brother. He also starred on Desperate Housewives in 2008. Weber appeared as a recurring guest on the 2008-09 season of the CBS crime drama Without a Trace.

He was recently part of the cast of the now cancelled ABC show Happy Town and had a major role in the TV movie A Fairly Odd Movie: Grow Up, Timmy Turner! in which he played the villain “Hugh J. Magnate Jr.” He stars occasionally in the live action comic Puddin’, alongside actor Eddie Pepitone. He narrated an unabridged audio book of Stephen King’s It. Between 2012 and 2017, Weber provided the voices of several characters on the Disney XD animated series Ultimate Spider-Man. In 2014, Weber rejoined former Wings co-star Rebecca Schull in Chasing Life in recurring character roles. In 2017, Weber made a guest appearance in the Curb Your Enthusiasm (episode: “The Shucker”). In 2020, he starred opposite Fran Drescher in the NBC comedy Indebted.