Look Back at Vintage Throwback Photos of Michael McKean and Annette O&x27;Toole on Their 27th Anniversary Stephanie SengweFri, March 20, 2026 at 10:30 AM UTC 0 Michael McKean & Annette O'TooleCredit: Derek Storm/FilmMagic 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.
Look Back at Vintage Throwback Photos of Michael McKean and Annette O'Toole on Their 27th Anniversary
Stephanie SengweFri, March 20, 2026 at 10:30 AM UTC
0
Michael McKean & Annette O'TooleCredit: Derek Storm/FilmMagic
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.
01 of 13
In the Beginning
Michael McKean & Annette O'TooleCredit: 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."
02 of 13
Meant to Be
Michael McKean and Annette O'TooleCredit: 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.
03 of 13
All in the Family
Annette O'Toole, Michael McKeanCredit: 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.)
04 of 13
How Adorable
Michael McKean and Annette O'TooleCredit: Bob Couey/Getty
O'Toole and McKean are pictured fawning over a river otter at SeaWorld's Haunted Lighthouse 4D movie premiere in 2003.
05 of 13
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Happy Days
Michael McKean and Annette O'TooleCredit: 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.
06 of 13
Flowers for You
Michael McKean & Annette O'TooleCredit: 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.
07 of 13
Major Love
Michael McKean and Annette O'TooleCredit: 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.
08 of 13
Adoring You
Michael McKean and Annette O'TooleCredit: Jeff Kravitz/FilmMagic
The Smallville actress grinned at her guy as they attended the Independent Spirit Awards in 2004.
09 of 13
New Looks
Annette O'Toole and Michael McKeanCredit: 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.
10 of 13
For the Greater Good
nnette O'Toole and Michael McKeanCredit: Matt Winkelmeyer/Getty
The musical duo were pictured on stage performing during the International Myeloma Foundation 10th Annual Comedy Celebration in 2016.
11 of 13
Forever and Ever
Annette O'Toole and Michael McKeanCredit: 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."
12 of 13
Still at It
Annette O'Toole and Michael McKeanCredit: Arturo Holmes/Getty
In 2025, they brought their comedic chops to the 2025 Writers Guild Awards New York Ceremony.
13 of 13
Match-y, Match-y
Annette O'Toole and Michael McKeanCredit: 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.
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Source: Entertainment
Published: March 20, 2026 at 12:46PM on Source: RED MAG
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