Gail was born in Detroit, Michigan, the son of Mary Elizabeth (Scanlon) and Maxwell Trowbridge Gail, Sr., a businessman, and he was raised in Grosse Ile, Michigan. He attended Williams College, and was later an instructor for the University Liggett School before becoming an actor. His acting debut came in 1970 for the Little Fox Theatre in San Francisco, California, playing Chief Bromden in the original stage production of One Flew Over the Cuckoo's Nest. In 1973, he reprised this role in his New York stage debut.
Gail is best known for his television role as Det. Stan "Wojo" Wojciehowicz in the sitcom Barney Miller (1975-1982). Gail's best known feature film role is in D.C. Cab (1983) as Harold, the owner of the D.C. Cab taxi company. He also directed several episodes of Barney Miller as Maxwell Gail. In 1984, Gail was featured in the monodrama The Babe on Broadway. This stage play was filmed and later featured on PBS. Gail has starred in other TV series including Whiz Kids (1983) as Llewellan Farley, Jr., an investigative reporter who is friends with a group of teenaged computer hackers. He worked on the short-lived Normal Life (1990). He has appeared on the TV series Sons & Daughters (2006).
Gail has made many guest appearances on TV shows such as: Walker, Texas Ranger (ep. Whitewater), Cannon, Dr. Quinn, Medicine Woman, Due South, The Streets of San Francisco, Paul Sand in Friends and Lovers, The Drew Carey Show, Hawaii Five-0, Quantum Leap, Psych, Gary Unmarried, NCIS episode "Murder 2.0", "Longmire" episode 40, Dexter, Mad Men, and Scorpion, and an episode of the FX miniseries Fargo. Gail appeared as Brooklyn Dodgers manager Burt Shotton in the 2013 film 42, a film about Jackie Robinson's first two years as a member of the Dodgers organization, including his first year of playing at the Major League level in 1947. Gail runs Full Circle, a production company which has featured documentaries on such subjects as Agent Orange, Native Americans, and nuclear issues. Gail was recast as Mike Corbin on General Hospital. He debuted on February 5, 2018.
