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The couple have supported one another during major career moments, but also weathered the initial COVID-19 lockdown together. And in Streisand's new memoir "My Name is Barbra," released in November, she shared more details about her relationship with Brolin.
Here's a timeline of Streisand and Brolin's iconic romance.
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July 1996: Streisand and Brolin were set up
James Brolin and Barbra Streisand in 1998.Ron Galella/Ron Galella Collection via Getty Images
November 1996: The couple made their red-carpet debut at the New York premiere of one of Streisand's films.
James Brolin and Barbra Streisand in 1996.Ron Galella/Ron Galella Collection via Getty Images
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March 1997: They attended the Oscars together.
James Brolin and Barbra Streisand at the 1997 Oscars.Russell Einhorn/Liaison
July 1998: Two years after their first date, Streisand and Brolin tied the knot.
James Brolin and Barbra Streisand in 1997.Ron Galella/Ron Galella Collection via Getty Images
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August 1998: The pair stepped out at Brolin's Hollywood Walk of Fame ceremony.
James Brolin and Barbra Streisand in 1998.FREDERICK M. BROWN/AFP via Getty Images
February 2001: Brolin was by Streisand's side when she was honored by the American Film Institute.
James Brolin and Barbra Streisand in 2001.Ron Galella, Ltd./Ron Galella Collection via Getty Images
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January 2003: Streisand attended the premiere of Brolin's film with him.
James Brolin and Barbra Streisand in 2003.Jon Kopaloff/Getty Images
2004: The couple made numerous public appearances together.
James Brolin and Barbra Streisand in 2004.Kevin Winter/Getty Images
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July 2007: The two traveled to France when Streisand was awarded the Légion d'Honneur.
Barbra Streisand and James Brolin at the 2007 Legion d'Honneur ceremony.Serge BENHAMOU/Gamma-Rapho via Getty Images
January 2011: Streisand and Brolin attended a state dinner together.
James Brolin and Barbra Streisand at the 2011 dinner at the White House.Brendan Smialowski/Getty Images
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July 2018: Streisand and Brolin celebrated their 20th anniversary.
Barbra Streisand and James Brolin in 2014.Sonia Moskowitz/Getty Images
July 2020: The pair celebrated another anniversary amid lockdown.
James Brolin and Barbra Streisand in 2015.Kevin Mazur/Getty Images
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November 2023: Streisand's memoir is released, and includes details about her relationship with Brolin.
James Brolin and Barbra Streisand at the 2019 Vanity Fair Oscars party.Kevin Mazur/VF19/WireImage