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In 2010, Harris directed a production of the rock musical Rent at the Hollywood Bowl; he cast his Beastly co-star Vanessa Hudgens as Mimi.65th Tony Awards on June 12, 2011, the 66th Tony Awards on June 10, 2012, and the 67th Tony Awards on June 9, 2013.

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He has played lead roles in a number of made-for-television features including Snowbound: The Jim and Jennifer Stolpa Story in 1994, My Ántonia in 1995, The Christmas Wish in 1998, Joan of Arc in 1999, The Wedding Dress in 2001, and The Christmas Blessing in 2005.

From 2005 to 2014, Harris played Barney Stinson, a serial womanizer, in the CBS ensemble sitcom How I Met Your Mother.

In 2014, Harris showed a more serious side in Gone Girl, directed by David Fincher.

Harris co-starred in the film as Desi Collings, the wealthy and obsessed ex-boyfriend of Amy Dunne, played by Rosamund Pike.

In 2004, he performed the dual role of the Balladeer and Lee Harvey Oswald on Broadway in the musical revival of Stephen Sondheim's Assassins.

He also sang the role of Charles (first played by Anthony Perkins) on the Nonesuch recording of Sondheim's Evening Primrose and portrayed Mark Cohen in the 1997 touring company of the musical Rent, a role he satirized on the January 10, 2009, episode of Saturday Night Live, which he hosted.

On television, he is known for playing the title character on Doogie Howser, M. (1989–1993), Barney Stinson on How I Met Your Mother (2005–2014, for which he was nominated for four Emmy Awards), and Count Olaf on A Series of Unfortunate Events (2017–).

Harris is also known for his role as the title character in Joss Whedon's musical Dr.

The role earned him Emmy nominations every year from 2007 to 2010.

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