Released in 1999, ‘Office Space‘ dives into the drudgeries of corporate life at a fictional software company, Initech, where three programmers orchestrate a plan to subtly pilfer from the firm, seeking respite from their mundane lives. Years after its release, we take a look at where three of its main stars — Ron Livingston, Stephen Root, and Gary Cole — have journeyed in their careers.

Ron Livingston

Known as the show’s main character, Peter Gibbons, Livingston portrayed a programmer longing for a shift in his life trajectory. Since ‘Office Space,’ Livingston has graced both big and small screens with a wide array of roles, from films such as ‘Adaptation‘ and ‘The Cooler‘ to HBO series like ‘Boardwalk Empire‘ and ‘Sex and the City.‘

2018 was active for Livingston with roles in ‘Tully,‘ ‘The Long Dumb Road,‘ ‘The Professor,‘ and ‘The Man Who Killed Hitler and Then the Bigfoot.‘ Notably, in 2023, he played a part in DC Studios’ ‘The Flash.’

Outside of his work, he married Rosemarie DeWitt in 2009, with whom he shares two daughters.

Stephen Root

In ‘Office Space,’ Root portrayed Milton Waddams, the often overlooked and mumbling Initech employee.

Before this role, Root was already known for his recurring role on ‘King of the Hill‘ and his film debut in ‘Crocodile Dundee II.‘ Following ‘Office Space,’ he engaged audiences in films like ‘Idiocracy,‘ ‘Trumbo,‘ ‘Get Out,‘ and TV shows including ‘Boardwalk Empire,‘ ‘True Blood,‘ and ‘Barry,‘ for which he received an Emmy nomination in 2019.

On a personal note, he has been married to actress Romy Rosemont since 2008 and has a child from a previous marriage.

Gary Cole

In ‘Office Space,’ Cole portrayed the monotone boss, Bill Lumbergh. Prior to his Lumbergh role, Cole had played Mike Brady in ‘The Brady Bunch Movie’ series and starred on NBC’s ‘Midnight Caller.‘

Since then, he’s been a familiar face on television with roles on ‘True Blood,‘ ‘Chuck,‘ ‘Entourage,‘ ‘Mixed-ish,‘ ‘The Good Wife,‘ and more. His role as political advisor Kent Davison on ‘Veep’ earned him an Emmy nomination.

Cole has also lent his voice talents to animated series like ‘Bob’s Burgers‘ and ‘Family Guy.‘ In his personal life, Cole was married to actress Teddi Siddal until her passing in 2018; they shared a daughter named Mary. He married interior designer Michelle Knapp in 2021.

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