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As many love stories go, Michael McKean and Annette O’Toole were friends for years they became an item.

These enduring lovebirds, who celebrate their 27th anniversary today, first crossed paths back in the ’70s. Nothing happened then, but then the fireworks immediately hit when they worked together on the set of 1998’s Final Justice. They wed the following year and have been locked in ever since. In addition to being spouses, the actors are also great collaborators and have worked together on numerous projects, including Smallville, on which O’Toole was a star.

Below, see the long-term couple’s relationship through the years as they celebrate their 27th wedding anniversary.

In the Beginning

Michael McKean & Annette O'Toole at the 1998 Hollywood Film Festival in Los Angeles.
Michael McKean & Annette O’Toole.Jeff Kravitz/FilmMagic, Inc

McKean and O’Toole knew each other for years before anything ever happened between them.

“Michael and I actually met many years ago when he was doing Laverne & Shirley,” the actress 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.”

Meant to Be

Married American actors Michael McKean and Annette O'Toole smile while embracing at the premiere of director Eric Schaeffer's film 'Wirey Spandell,' Los Angeles, California.
Michael McKean and Annette O’Toole.Chris Bergman/Fotos International/Getty

Sparks started flying during their time working togethr on Lifetime’s Final Justice 1998. O’Toole told TheaterMania that she knew McKean was into her during one specific phone call.

“I heard it all in his voice,” she recalled. “I just heard that he liked me that way.”

McKean confirmed: “I think what you heard in my voice was, ‘I’m going all in here.'”

O’Toole then revealed she had a gleeful moment in private. “I did something I had only seen in movies. I put the phone down. I said, ‘I really, really want to talk to you but Anna’s so sick. Could we talk tomorrow?’,” she explained, referring to her daughter from her previous marriage to Bill Geisslinger.

“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.”

The rest is history and the couple wed on March 20, 1999.

All in the Family

Annette O'Toole, Michael McKean and children during Premiere of "Small Soldiers" at Universal Ampitheater in Los Angeles, California, United States.
Annette O’Toole, Michael McKean.Ron Galella, Ltd./Ron Galella Collection via Getty

In 1998, the couple hit the premiere of Small Soldiers with their blended family. In addition to Anna, O’Toole shares daughter Nell with her ex-husband. McKean was also previously married and he welcomed sons Colin and Fletcher with ex-wife Susan Russell. (Colin, who was an actor, died of a heroin overdose in 2012.)

How Adorable

Actors Michael McKean and Annette O'Toole greet a river otter at SeaWorld's Haunted Lighthouse 4-D movie premiere May 17, 2003 at San Diego's SeaWorld.
Michael McKean and Annette O’Toole.Bob Couey/Getty

O’Toole and McKean are pictured fawning over a river otter at SeaWorld’s Haunted Lighthouse 4D movie premiere in 2003.

Happy Days

Michael McKean and wife Annette O'Toole arrive for the Friars Club Roast of Rob Reiner at the New York Hilton.
Michael McKean and Annette O’Toole.Richard Corkery/NY Daily News Archive via Getty

The smiling couple was snapped heading into the Friars Club Roast of Rob Reiner at the New York Hilton in 2000.

Flowers for You

Michael McKean & Annette O'Toole during "A Second Hand Memory" Off-Broadway Opening Night at Atlantic Theater Comany in New York City, New York, United States.
Michael McKean & Annette O’Toole.Derek Storm/FilmMagic

O’Toole looked smitten as she proudly supported her husband during the opening night of A Second Hand Memory on Broadway back in 2004.

Major Love

Actor Michael McKean and actress Annette O'Toole attend the 76th Annual Academy Awards at the Kodak Theater on February 29, 2004 in Hollywood, California.
Michael McKean and Annette O’Toole.Carlo Allegri/Getty

The pair shared a smooch while attending the 76th Annual Academy Awards in 2004. They were nominated for a Best Original Song Oscar for “A Kiss At the End of the Rainbow,” which they wrote for the film A Mighty Wind.

Adoring You

Michael McKean and Annette O'Toole during 2004 Independent Spirit Awards - Arrivals at Santa Monica Pier in Santa Monica, California, United States.
Michael McKean and Annette O’Toole.Jeff Kravitz/FilmMagic

The Smallville actress grinned at her guy as they attended the Independent Spirit Awards in 2004.

New Looks

Annette O'Toole and Michael McKean attend The Public Theater's "King Lear" opening night after party at Chinatown Brasserie on November 8, 2011 in New York City
Annette O’Toole and Michael McKean.Steven A Henry/WireImage

The pair debuted new looks as O’Toole showcased a shorter cut, while McKean rocked a full beard which he grew for his turn as Earl of Gloucester in King Lear, back in 2011.

For the Greater Good

Actors Annette O'Toole (L) and Michael McKean perform onstage during the International Myeloma Foundation 10th Annual Comedy Celebration at the Wilshire Ebell Theatre on November 5, 2016 in Los Angeles, California.
nnette O’Toole and Michael McKean.Matt Winkelmeyer/Getty

The musical duo were pictured on stage performing during the International Myeloma Foundation 10th Annual Comedy Celebration in 2016.

Forever and Ever

Annette O'Toole and Michael McKean attend MPTF's Lights, Camera, Take Action! Caring for Hollywood's Crews Telethon at KTLA 5 on December 09, 2023 in Los Angeles, California.
Annette O’Toole and Michael McKean.Michael Kovac/Getty

The couple told Vanity Fair that one of their favorite pastimes is reading to each other.

“Michael has a very mellifluous voice,” O’Toole 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.”

Still at It

Annette O'Toole and Michael McKean speak onstage during the 2025 Writers Guild Awards New York Ceremony at Edison Ballroom on February 15, 2025 in New York City.
Annette O’Toole and Michael McKean.Arturo Holmes/Getty

In 2025, they brought their comedic chops to the 2025 Writers Guild Awards New York Ceremony.

Match-y, Match-y

In this handout photo provided by The Academy, Annette O'Toole and Michael McKean pose backstage during the 98th Oscars Governors Ball at Dolby Theatre on March 15, 2026 in Hollywood, California.
Annette O’Toole and Michael McKean.Mike Baker / The Academy via Getty

The couple of 27 years attended the 2026 Oscars (where he participated in the tribute to Rob Reiner) perfectly in step.