(written from a Production point of view)
Cobbs is perhaps best known for playing the role of Reginald, a retiring night watchman and antagonist in the 2006 film Night at the Museum. He later reprised this role in the 2014 sequel Night at the Museum: Secret of the Tomb.
Cobbs has made numerous film and television appearances. One of his earliest motion pictures was 1977's Greased Lightning, which also featured Noble Willingham. Cobbs and Willingham co-starred together again in 1994's The Hudsucker Proxy, along with Roy Brocksmith and Mike Starr. He and Starr previously appeared in the 1987 film Five Corners and 1992's The Bodyguard.
In 1978, Cobbs appeared as a bartender in A Hero Ain't Nothin' But a Sandwich, starring Paul Winfield. He later played a bartender in the 1983 comedy Trading Places, which also featured Ron Taylor. Cobbs also appeared in 1983's Silkwood with Bruce McGill and Jim Beaver and had a supporting role in 1986's The Color of Money, in which Iggy Pop appeared, as well. In 1988, Cobbs appeared in Clint Eastwood's Bird, as did Star Trek: Voyager star Tim Russ (Tuvok) as well as Trek guest actors Hamilton Camp and Tony Todd. He was also a regular on the short-lived TV series The Slap Maxwell Story, co-starring Megan Gallagher.
Cobbs co-starred with Bob Gunton in the 1993 science fiction action film Demolition Man and in the 1995 TV movie Kingfish: A Story of Huey P. Long. Cobbs also had a role in the 1995 made-for-TV science fiction comedy Out There, which co-stars the likes of Carel Struycken, Paul Dooley, and, in an uncredited cameo, Robert Picardo. Cobbs and Paul Dooley both also appeared in the 2003 film A Mighty Wind.
Other films Cobbs appeared in include New Jack City (1991, with Tina Lifford, and Christopher Michael), Things to Do in Denver When You're Dead (1995, with Christopher Lloyd, Tommy "Tiny" Lister, Jr., and Bill Bolender), Fluke (1995, with Ron Perlman), That Thing You Do! (1996, with Clint Howard), and Ghosts of Mississippi (1996). That last film also featured Trek actors Whoopi Goldberg, Susanna Thompson, Bill Smitrovich, Terry O'Quinn, Richard Riehle, Brock Peters, and Thomas Kopache. Cobbs and Susanna Thompson also appeared in 1999's Random Hearts. In 1998, Cobbs appeared in the film Paulie, along with ENT guest actor Bruce Davison, and in I Still Know What You Did Last Summer, with frequent Trek guest actor Jeffrey Combs and another Star Trek: Deep Space Nine guest star, Benjamin Brown. Some of Cobbs' more recent films include 2002's Sunshine State with Miguel Ferrer and Enough with Bruce French and Jeff Kober.
Cobbs played the role of Tony in several episodes of The Drew Carey Show from 2002 through its end in 2004. Actor Diedrich Bader was a regular on this series.