The 5 oldest winners of Big Brother

Big Brother has proven to be more of a young person’s game with the vast majority of the show’s winners over the 26 seasons of the summer hit falling in the age 21 to 27 range, but there have been a handful of older players who have ended up winning in the end.

After this 26th season of Big Brother comes to an end, 22 of the show’s 26 winners will have been between the ages 21 and 29, with just four of the winners being aged 30 and up and just one winner over age of 40.

This hit show from CBS has had its share of “older” players. Including four in the last two seasons with Big Brother 25’s Cirie Fields (53) and Felicia Cannon (63), and Big Brother 26’s Kenny Kelley (52) and Angela Murray (50).

The oldest contestant ever on Big Brother was Jerry MacDonald (75) who ended up finishing in third place on Big Brother 10 where the retired Marine captured two Head of Households (HoH) and two Power of Vetos (PoV) in his 66 days in the house. Jerry was nominated five times and was ultimately voted out by eventual winner Dan Gheesling in the Final 3.

Jerry had another older HouseGuest playing with him in BB10 in Reny Martin (53). Other notable players over 50 who have been in the reality competition show include 55-year-old Kevin Schlehuber (Big Brother 19, 4th place), 50-year-old Glenn Garcia (Big Brother 18, first evicted on Day 2), and 51-year-old Gerry Lancaster (Big Brother 3, evicted day 55).

Here are the five oldest winners in Big Brother history.

“Evel Dick” Donato, 44, Big Brother 8

The oldest winner ever on Big Brother was Dick Donato who was 44 years old when he entered the house on Big Brother 8. Nicknamed Evel Dick from an email account address he once created, he ended up defeating his daughter Daniele—who was 20 when she entered the house and 21 on finale night—by a 5-2 vote to win the $500,000 grand prize.

Evel Dick, now 61, also was a cast member on Big Brother 13 but had to leave the show early when he was found to be HIV-positive by the medical staff of the hit summer show. He also was on Season 5 of Couples Therapy (VH1) and is a podcaster who created the popular Big Brother recap show he hosts called Dick at Nite.

This summer, Dick packed up his cats and moved from Florida to Ireland.

Mike “Boogie” Malin, 35, Big Brother 7

The second-oldest winner of Big Brother is Mike “Boogie” Malin, who at age 35 won his second time around as a contestant with his loyal ally and show legend, Will Kirby on Big Brother 7.

On Big Brother 2, the Los Angeles bar owner finished in 8th place and was evicted on Day 33 at age 30 in the classic season which saw his ally Dr. Will emerge victorious. Five years and five seasons later, Boogie made it all 72 days and won on finale night on Big Brother 7: All-Stars, beating runner-up Erika Landin.

Boogie would also return as one of the coaches and later a player on Big Brother 14 where he was evicted on Day 48 at the age of 41—the oldest contestant in the house that season along with 41-year-old Joe Arvin.

Kaycee Clark, 30, Big Brother 20

The oldest female to win Big Brother was Kaycee Clark, who won Big Brother 20 at age 30. Born on Dec. 26, 1987, the then professional football player from San Diego, California defeated Tyler Crispen in the Final 2 by a narrow 5-4 vote and took home the $500,000 grand prize.

Kaycee, who is now in a serious relationship and is engaged to Nany Gonzalez from The Challenge (MTV), has also competed in five seasons of The Challenge and won in Season 37 when she competed with Chris “CT” Tamburello on The Challenge: Spies, Lies and Allies.

Derrick Levasseur, 30, Big Brother 16

The third-oldest male winner of Big Brother was Big Brother 16 winner Derrick Levasseur who had no votes against him the season he beat ally and eventual show winner Cody Calafiore by a 7-2 vote.

The Providence, Rhode Island native—now age 40—was born on Feb. 3, 1984 and won HoH four times on BB. Like Evel Dick, Derrick now hosts a Big Brother podcast with Cody called The Winner's Circle.

Adam Jasinski, 29, Big Brother 9

Although he was under age 30 when he won Big Brother 9 (29), Adam Jasinski is the fifth-oldest winner of the show as he beat ally Ryan Quicksall in the Final 2 by a 6-1 vote.

Adam won HOH twice (Week 6 and 8) and one PoV (Week 9), but somehow charmed his way to the $500,000 which he used in the wrong way as part of a drug ring. Adam, now 46, was arrested in 2009 and spent four years in prison and then got clean and became an addiction recovery consultant.