(written from a Production point of view)
Holmes R. Osborne (born 7 August 1947; age 73) is the Kansas City born actor who appeared as an Enolian official in the Star Trek: Enterprise second season episode "Canamar". His costume was later sold off on the It's A Wrap! sale and auction and was previously worn by Louis Ortiz in the episode "Resistance".  
He had a recurring roles as President Robert Maxwell on the science fiction series Seven Days and on the sci-fi series Invasion, playing Mayor Littles. He also played a mayor in an episode of Boston Legal, starring William Shatner, Rene Auberjonois, and Henry Gibson. He and his "Canamar" co-star Mark Rolston had roles in the acclaimed 1998 mini-series From the Earth to the Moon, as did fellow Star Trek alumni David Clennon, Ronny Cox, Clint Howard, Daniel Hugh Kelly, Andy Milder, Ethan Phillips, Harve Presnell, Stephen Root, and Alan Ruck.
He and fellow Enterprise guest Dey Young played a married couple in the 1999 film The Mod Squad, based on the TV series starring Clarence Williams III and Tige Andrews. Osborne also had roles in such popular films as That Thing You Do (1996, with Bill Cobbs), Election (1999, with Matt Malloy), Bring It On (2000, starring Kirsten Dunst and Gabrielle Union), Identity (2003), and Anchorman: The Legend of Ron Burgundy (2004). His largest role to date was in the acclaimed 2001 sci-fi thriller Donnie Darko, in which he played the father of the title character.