Sher has directed revivals of classic mid-century musicals on Broadway at Lincoln Center, which include South Pacific (2008), The King and I (2015), My Fair Lady (2018), and Camelot (2023).

)[8][9] His productions at Intiman have included: At the Theatre for a New Audience (TFANA) in New York, Sher directed productions of[15] Waste by Harley Granville Barker in 2000 (its American premiere, winning the 2000 Obie Award for Best Play), Cymbeline by Shakespeare in 2002, Dom Juan by Molière in 2003, and Pericles, Prince of Tyre by Shakespeare in 2004.

In 2006 Sher directed Gioachino Rossini's Il barbiere di Siviglia (The Barber of Seville) at the Metropolitan Opera in Lincoln Center.

[17][18] In March 2011, Le Comte Ory by Rossini opened at the Metropolitan Opera in New York, in a production directed by Sher.

"[19] In June 2011, Sher's production of the world premiere of Nico Muhly's Two Boys was presented at the English National Opera.

Sher directed a London revival of Kiss Me Kate at the Barbican Theatre for a run lasting from June through September 2024.

[20][21] Sher made his Broadway debut in 2005 when his production of The Light in the Piazza which had originated at the Intiman Playhouse premiered at the Vivian Beaumont Theatre.

In 2010 Sher directed a musical production of Women on the Verge of a Nervous Breakdown based on the 1988 film by Pedro Almodóvar.

[22] A previously announced revival of Funny Girl that Sher was expected to direct with a Broadway opening in February 2012 was ultimately postponed.

[33] Sher received Tony Award nominations for Oslo, a 2018 revival of My Fair Lady, and the 2018 play adaptation of To Kill a Mockingbird.

[2] His father, an insurance broker whom he described to The New York Times as a "brilliant businessman, very charismatic", was also a serial philanderer who had a second family with another woman.

His mother soon met a Chinese-American man, Doug Chung, who moved in, helped rear the family and brought them much needed stability.