In a city known for fleeting romances and fast-paced lives, there are rare moments when Hollywood pauses to honor something real—something lasting.

That moment arrived on October 28 at The Plaza in New York City when Michael McKean and Annette O’Toole, one of Hollywood’s most enduring and beloved couples

, graced the red carpet at the Season 2 premiere of Netflix’s critically acclaimed political thriller The Diplomat.

McKean, now 77, portrays the authoritative and commanding President William Rayburn on the hit series. But all eyes weren’t just on his character that evening. Walking beside him, hand-in-hand, was his wife of 25 years, Virgin River star Annette O’Toole, 72, radiating grace in a soft cream blouse and sleek pantsuit. Together, they didn’t just arrive at the premiere—they stole the show.

A Romance Decades in the Making

To understand the power of their presence, one must first know the magic of their love story. McKean and O’Toole may be longtime Hollywood veterans, but their romance is a relatively late chapter in both of their lives. Though their paths first crossed in the 1970s—each carving out their own successful careers in film, television, and theater—it wasn’t until 1998, on the set of the Lifetime movie Final Justice, that their story truly began.

What started as an on-screen partnership blossomed into a whirlwind connection. Their first date? A benefit concert featuring legends like Bob Dylan, Joni Mitchell, and Van Morrison—an evening that would leave an indelible mark on O’Toole’s heart.

“I would have married him that day,” she later confessed in an emotional 2018 interview with TheaterMania, reflecting on the night her life changed forever.

By March 1999, they were husband and wife, sealing a bond that would prove to be as creatively fruitful as it was deeply personal.

From Co-Stars to Lifelong Collaborators

While many Hollywood couples maintain separate professional identities, McKean and O’Toole thrive in collaboration. Their creative synergy has gifted fans with some of the most charming and memorable performances across TV and film. One of their early public fan-favorite moments was McKean’s guest role on Smallville, where O’Toole played Martha Kent, Superman’s nurturing adoptive mother.

The pair brought quirky comedy to Boy Meets World as Topanga’s eccentric parents, and in 2003, their musical talents stole the spotlight in A Mighty Wind, the beloved mockumentary directed by Christopher Guest. There, they co-wrote and performed the tender folk ballad “A Kiss at the End of the Rainbow,” earning them an Academy Award nomination for Best Original Song.

Their music career didn’t end there—they contributed to Disney’s World of Happiness album and continue to write music together, proving that their partnership extends far beyond the stage and screen.