Annette O’Toole and Michael McKean have been married since 1999

Annette O’Toole and Michael McKean have one of Hollywood’s enduring love stories.

Both actors with long résumés, the pair had been acquaintances in the 1970s before

reconnecting on a film set in 1998 and getting married in 1999. On March 20, 2022, McKean celebrated their 23rd wedding anniversary with a sweet message to O’Toole on X (formerly Twitter). “23 years ago, I married my best friend and it is working out beautifully. Thanks for saying yes,” he wrote.

McKean has long been known for his offbeat comedic style in Christopher Guest movies like Best in Show and A Mighty Wind while O’Toole is beloved from her time on Smallville and Nash Bridges. She currently stars in Virgin River, which is now in its fifth season. The pair have even collaborated on the movie Final Justice and  TV show Boy Meets World.

In a 2022 interview with Hello!, O’Toole and McKean gave a tour of their Los Angeles home, sharing why it works for their relationship. O’Toole said the living room is the size of a “mini ballroom, perfect for the outsize personalities the entire household seems blessed with. We sing, dance, make music … try and stop us.”

O’Toole has also shared the secret to her long marriage with McKean. “We really like spending time together,” she told Vanity Fair in 2022.

Here’s everything to know about Michael McKean and Annette O’Toole’s marriage.

They’re both known for iconic movie and  TV roles

McKean first rose to fame on Laverne & Shirley, which ran from 1976 to 1983, around the same time he first met O’Toole. Since then, he’s been a series regular on Saturday Night Live, Better Call Saul and The Diplomat among others, in addition to acting in movies including Weird: The Al Yankovic Story and Broadway shows like Hairspray

O’Toole has been a major part of television programming since the ’90s, including the miniseries It, based on Stephen King’s novel, and has continued her career in shows like The Huntress and The Punisher. O’Toole has also appeared in movies like 48 Hrs. and Superman III.

They met decades before they were romantically involved

In the 1970s, McKean and O’Toole were friendly, but not close. She recalled in a 2018 video for TheaterMania that they’d often run into each other at parties thrown by actors like Rob Reiner and Ed Begley Jr.

“Michael and I actually met many years ago when he was doing Laverne & Shirley,” O’Toole told Soundtrack.net in 2004. “I was this actress, and we could bump into each other at various screenings; we had friends in common, but we didn’t really know each other very well. We had very different lives.”

O’Toole and McKean fell in love on a movie set

When the two were both cast in the 1998 Lifetime movie Final Justice, they reconnected — and sparks flew during filming.

One night, O’Toole told TheaterMania, McKean called her while she was taking care of her daughter Anna from her first marriage to Bill Geisslinger. “I heard it all in his voice,” O’Toole recalled. “I just heard that he liked me that way.”

McKean interjected, “I think what you heard in my voice was, ‘I’m going all in here.’ “

“And I did something I had only seen in movies,” the actress continued. “I put the phone down. I said, ‘I really, really want to talk to you but Anna’s so sick. Could we talk tomorrow?’ He said, ‘Yeah, I’ll call you tomorrow.’ I thought, he’s never going to call me tomorrow. But I put the phone down and I went into the bathroom and jumped up and down in silent screaming.”

They had their first date at a benefit concert where Bob Dylan, Joni Mitchell and Van Morrison played. “I would have married him that day,” O’Toole said with tears in her eyes. The pair tied the knot in March 1999.

“As a gag, I told her, ‘And they said it wouldn’t last,’ but nobody said that,” McKean recalled to TheaterMania. “They were like, ‘Of course, duh.’ “

They’re both musicians

McKean has had a long career of writing songs for movies, but it wasn’t until 2001 that O’Toole joined him in playing with melodies. The pair worked together on three songs for the movie A Mighty Wind during a long drive from Los Angeles to Vancouver.

“Michael has had this collaboration with other people over the years, but this is my very first time ever doing it,” the actress told Soundtrack.net in 2004. “So every time we write one, it just gives me more confidence to do the next.”

O’Toole and McKean have worked together many times

McKean was a guest star on three episodes of Smallville during its 10-season run, in which O’Toole played Clark Kent’s mother. They’ve also appeared together as Topanga’s parents on Boy Meets World.

O’Toole and McKean have continued to collaborate on music, too. In 2004, the couple had a song of theirs included on a Disney album called World of Happiness.

“We wrote a song for it called ‘What Could Be Better?’ and we actually wrote it while on the set of Smallville,” O’Toole told Soundtrack.net. “That’s the goal — to be those people you can call when you need a song for this movie, or this performer. We have a backlog now of songs, building up a library!”

They were nominated for an Oscar together

The duo’s work on songs for A Mighty Wind earned them an Oscar nomination.

In the film about 1960s musicians, McKean appeared as a member of the fictional band the Folksmen. O’Toole didn’t have a role in the movie, but she did play an important part, working with her husband to write the movie’s biggest song, “A Kiss At the End of the Rainbow.”

In the movie, Eugene Levy and Catherine O’Hara perform the tune. McKean and O’Toole were nominated for an Oscar for Best Original Song at the 2004 Academy Awards.

They have a sweet bedtime ritual

O’Toole and McKean told Vanity Fair in 2022 that they read to each other every night — even when they’re in different locations.

“Michael has a very mellifluous voice,” the actress said. “I get up really early in the morning, so, I’m really tired by the end of the night, and his voice completely puts me to sleep, not because I’m bored, but because it’s so soothing.”