The 76-year-old singer sent a sweet message to Brolin on their wedding anniversary Sunday.
Streisand shared a photo of herself with the 77-year-old actor that was taken at the Los Angeles premiere of Sicario: Day of the Soldado last week. Josh Brolin, Brolin's son with ex-wife Jane Cameron Agee, stars in the new movie.
"Has it really been 22 years since our blind date @jamesbrolin_? Married for 20 years. Happy anniversary honey. Bee. X," Streisand captioned the picture.
Streisand recalled her first date with Brolin in an interview with W in 2016.
"I met him at a dinner and expected and bearded mountain-man type, and he had cut off all his hair and was clean-shaven. I asked him, 'Who screwed up your hair?' He later told me that's when he fell in love with me. My fella likes to hear the truth, which is unusual."
Streisand and Brolin married in July 1998 at the singer's home in Malibu. Streisand was previously wed to Elliot Gould and is parent to son Jason Gould with the actor. Brolin is also parent to son Jess Brolin with Agee and to daughter Molly Brolin with ex-wife Jan Smithers.