Along with numerous independent and small-budget film roles, he played supporting characters in box-office hits Grumpy Old Men (1993), Flubber (1997), Rumor Has It (2005), The House Bunny (2008) and About Last Night (2014).

McDonald has portrayed several notable real-life people, including game show host Jack Barry in Quiz Show (1994), mountaineer Jon Krakauer in Into Thin Air: Death on Everest on ABC (1997), sportscaster Mel Allen in the HBO film 61* (2001), Yankee legend Joe DiMaggio in ESPN's The Bronx Is Burning (2007), U.S. Attorney General Harry M. Daugherty on HBO's Boardwalk Empire (2010–2012), Texas revolution soldier Henry Karnes in History Channel's Texas Rising (2015), and Clinton lawyer Robert S. Bennett on FX's Impeachment: American Crime Story (2021).

In 2022, McDonald was nominated for a Primetime Emmy Award for Outstanding Guest Actor in a Comedy Series for his role as casino CEO Marty Ghilain on the HBO Max show Hacks.

He graduated from Romulus Central School in 1973[11] and later earned a degree from Hobart College in Geneva, New York where he played football and soccer.

His credits include Grease 2 (1982), Breakin' (1984), Where the Boys Are '84 (1984), The Boys Next Door (1985), Outrageous Fortune (1987), Thelma & Louise (1991), Fatal Instinct (1993), Grumpy Old Men (1993), Quiz Show (1994), the HBO film The Tuskegee Airmen (1995), Happy Gilmore (1996), Celtic Pride (1996), House Arrest (1996), Flubber (1997), Dirty Work (1998), The Faculty (1998), The Skulls (2000), The Perfect Storm (2000), Spy Kids 2: The Island of Lost Dreams (2002), Broken Flowers (2005), Rumor Has It (2005), American Pie Presents: The Naked Mile (2006), American Pie Presents: Beta House (2007), and Superhero Movie (2008).

He portrayed mountaineer Jon Krakauer in the ABC film Into Thin Air: Death on Everest (1997), famous baseball broadcaster Mel Allen in the HBO film 61* (2001), baseball player Joe DiMaggio in the ESPN original series The Bronx Is Burning (2007) and U.S. Attorney General Harry M. Daugherty on HBO's Boardwalk Empire (2010–2012).

[21] In 2021, McDonald joined the cast of Hacks on HBO Max as Las Vegas casino owner Marty Ghilain, where he was nominated for a Primetime Emmy Award for Outstanding Guest Actor in a Comedy Series for his role.