Miss Congeniality captured audiences when it debuted on December 22, 2000. Sandra Bullock starred as Grace Hart, an undercover agent posing as Miss New Jersey Gracie Lou Freebush in a national beauty pageant. Although she didn’t win, she was the hero of the story.
This December 22 marks the 25th anniversary of the cherished film. Since its release, the cast of Miss Congeniality has appeared in numerous successful films and some have even won Oscars. Here’s a look at where they are now.
Sandra Bullock

Sandra Bullock, now 56, portrayed Grace Hart in the 2000 comedy. Her performance earned her a Golden Globe nomination for Best Actress in a Musical or Comedy. She reprised her role in the 2005 sequel.
Over the years, Sandra has appeared in successful comedies like Two Weeks Notice, The Proposal, and The Heat. She showcased her dramatic skills in the 2009 film The Blind Side, winning an Oscar for Best Actress. Her other notable films include Gravity, Murder by Numbers, and Bird Box.
Sandra has had relationships with Tate Donovan, Ryan Gosling, and Matthew McConaughey. She married Monster Garage host Jesse James in 2005, but they divorced in 2010 amid infidelity allegations. She has adopted two children and has been dating photographer Bryan Randall since 2015.
Benjamin Bratt

Benjamin Bratt, also 56, played Eric Matthews, Sandra’s on-screen love interest. He did not appear in the sequel. Bratt is known for roles in both live-action and animated films, including Traffic, Catwoman, and Piñero. He voiced characters in Cloudy with a Chance of Meatballs, Coco, and Despicable Me 2.
On television, Bratt portrayed Javier Delgado in Modern Family, Dr. Jake Reilly in Private Practice, and Steve Navarro in 24: Live Another Day.
At the time of Miss Congeniality‘s release, Bratt was dating Julia Roberts. They parted ways in 2001. He married Talisa Soto in 2002, and they have two children.
Michael Caine

Sir Michael Caine, 87, is a celebrated actor with a career spanning six decades. He played Victor Melling, the pageant coach, in Miss Congeniality but did not return for the sequel.
In the same year as Miss Congeniality, Caine won his second Oscar for Best Supporting Actor. He earned another nomination for The Quiet American in 2002. He gained further fame as Alfred in Christopher Nolan’s The Dark Knight trilogy.
Caine has appeared in several of Nolan’s films, including Inception, Interstellar, The Prestige, and Tenet. Other films include Now You See Me and Kingsman: The Secret Service.
Candice Bergen

Candice Bergen, 74, portrayed the antagonist Kathy Morningside. Bergen, already an acclaimed actress, continued her career with roles in Sweet Home Alabama, The Women, Bride Wars, and Book Club.
She joined Boston Legal in 2005, playing Shirley Schmidt, reuniting with co-star William Shatner. Her performance earned Emmy nominations.
Bergen reprised her role in the 2018 Murphy Brown reboot, which was canceled after one season. Her latest work includes the 2020 film Let Them All Talk.
William Shatner

William Shatner, 89, played pageant host Stan Fields and returned for the sequel. Best known as Captain Kirk in Star Trek, Shatner has had a diverse career.
He portrayed Danny Crane in The Practice and Boston Legal, winning two Emmys. Other TV roles include Better Late Than Never and Shatner’s Raw Nerve. He has also appeared in advertisements for DirecTV and Priceline.
Heather Burns

Heather Burns, 45, portrayed Miss Rhode Island Cheryl Frasier, a friend to Grace. She reprised her role in the 2005 sequel and reunited with Sandra in Two Weeks Notice.
Burns has appeared in films like Manchester by the Sea and Bewitched. She recently played Mary Moskowitz McCutcheon in The Politician season two.