What These Big Brother Winners Look Like Today

Big Brother has had its ups and downs over its long run, but the reality TV series has remained a giant of the genre for many years thanks to its fun voting format and addicting live feeds. Although the ability to watch the houseguests 24/7 has set Big Brother apart from other reality competition shows, what really makes the series stand out is its memorable and often wild contestants. 

While many contestants make their impression on the show's fans, only one person gets to take home the $500,000 prize each season. Fans love to debate which winners are the best and who actually deserved the top dollar, but the fact of the matter is that every summer, for better or for worse, one person leaves the Big Brother house half a million dollars richer.

What those winners do with their newfound cash and fame has varied quite a bit. Some have gone into business, while others have stuck around the reality realm and continued to make a name for themselves in television. Still others have made unexpected journeys in their careers and personal lives. Here's what the lives of these memorable Big Brother winners look like today.

Will Kirby

Will Kirby put Big Brother on the map with his impressive strategic game and memorable Diary Room sessions, all of which culminated in a win for him in the show's second season, which was the first season to feature house guests voting each other off the show. Kirby would later return to the series for Big Brother All-Stars, placing fourth. He has also popped up on subsequent seasons for guest appearances, hosting multiple jury roundtables. 

Kirby has booked some other on-screen appearances as well. He voiced himself on an episode of Robot Chicken and also played himself on episodes of Youthful Daze, The Young and the Restless, and Cold Turkey. He appeared on multiple episodes of The Price is Right and has stopped by shows such as The Talk, The Real Housewives of Orange County, The Doctors, and Dr. 90210. He also competed on 2005's Battle of the Network Reality Stars.

Much of Kirby's life after the show has been devoted to his medical practice. He runs a dermatology practice in California and works as an assistant professor of dermatology at Western University of Health Science and Nova Southeastern University. He made headlines in April 2018 when he reportedly put his doctor skills to good use, rendering aid to not one, but two moviegoers who suffered seizures during different films on the same night.

Kirby has settled down since Big Brother, getting engaged in 2011 to Erin Brodie, winner of the 2003 reality show For Love or Money, and finally tying the knot in 2017, after the pair had two children together.  

Jun Song

Jun Song may have gotten some heat for her floater strategy on Big Brother Season 4, but she also brought home $500,000. Since the show ended, Song has relocated to Ghent, Belgium, where her ex-husband, Davy Goethals, worked as a dock worker. The pair, who met while Song was on vacation in the Dominican Republic, have one son.

Song was working on Wall Street when she took part in Big Brother, but she lost her job during the 2008 financial crisis. She says that she debated what to do with her life after that, but when she met Goethals on vacation, she decided to chart a new course. Song wound opening an authentic Korean food restaurant in Ghent in 2014, but the restaurant reportedly closed its doors in September 2017. Song also wrote on her blog that she and Goethals were "heading towards divorce" around that time.

Song has stopped by Big Brother a few times over the years to help out with competitions, and she has also appeared on Yes, Dear and VH1 Goes Inside. She's been active on Twitter and has a blog where she frequently shares very personal updates on her life and, of course, the latest Big Brother news. 

Mike 'Boogie' Malin

Mike "Boogie" Malin has played Big Brother three times, starting in Season 2, when his Chilltown alliance member Will Kirby ultimately took home the prize. Malin was able to come out on top the next time he cometed, winning Big Brother: All-Stars. He later returned for Season 14 as a coach, although the coaches ultimately became house guests and Malin wound up placing tenth.

Malin has continued to pop up onscreen since winning Big Brother, appearing as himself in Reality Obsessed, The Talk, Reality Remix, Dr. 90210, and Battle of the Network Reality Stars. He ventured into acting, appearing on Monk, The Parkers, Jack and Jill, Hood of Horror, Robbie's Brother, Fishes, and Gun. 

Most of Malin's energy since the show ended has been focused on his business ventures, although his entrepreneurial spirit has attracted a great deal of controversy. Malin has been sued and has filed suits related to extortion and embezzlement surrounding his restaurateur business, and in 2015, TMZ reported that he was about $23 million in debt. Malin's business partners reportedly accused him of using company money "to have multiple sexual encounters with various older men during which Malin would live out fetish role play fantasies." Malin was ordered to pay $800,000, reported TMZ.  

Dick 'Evel Dick' Donato

Dick "Evel Dick" Donato was a controversial player on Big Brother's eighth season, mostly thanks to his unabashed and uncensored gameplay. Although he rubbed some people the wrong way with his wild antics, Donato still managed to earn enough votes to bring home the $500,000, beating his own daughter, Daniele Donato, for the top prize.

Dick later returned to the show for its thirteenth season, but he was pulled from the game early. He revealed in a 2014 appearance on Couples Therapy that he left the show after a blood test done by producers revealed that he was HIV positive. Dick said he decided to go public with his diagnosis after three years because he realized he had a platform to "remind viewers to get tested [and] practice safe sex."

Evel Dick has remained active in the Big Brother community, hosting the talk show Dick at Nite, which brings on former contestants from Big Brother, Big Brother Canada, Survivor, and more. He has also been active on Twitter and frequently interacts with fans via social media. 

Adam Jasinski

Adam Jasinski took home the win in Big Brother's controversial ninth season, which aired in the winter due to the 2007-08 Writers' Strike. Jasinski came under fire in the house for comments he made about mentally ill people, and he has continued to stir up controversy since he won that half-million dollars.

When Jasinski won, he claimed he planned to give a fifth of the money to charity and use the rest to start a business. He apparently never gave away the cash, but he did start a business — a, um, pharmaceutical business. According to Entertainment Weekly, Jasinski was arrested after trying to fly from Florida to Massachusetts with oxycodone pills in his carry-on bag in October of 2009. 

He pleaded guilty to one count of possession with intent to distribute oxycodone and was sentenced to 48 months in prison. He actually took down another former Big Brother player as well. Matt McDonald was sentenced to 36 months in prison on charges of conspiracy to possess with the intent to distribute oxycodone. 

Jasinski later opened up about his addiction to painkillers in an extensive interview with Entertainment Weekly, saying that he started using after a car accident in college. He said he even snuck OxyContin into the Big Brother house, although producers confiscated it during the second week of the game. Jasinski, who claimed he also struggles with bipolar disorder, launched a rehab facility with his mother in 2016 and is working to self-publish rehab books.

Dan Gheesling

Dan Gheesling is widely considered one of Big Brother's best strategic players for his work on the show's tenth season, which saw him taking home the prize over his friend and alliance member Memphis Garrett. Gheesling returned for the show's fourteenth season, managing to save himself from elimination by infamously planning his own Big Brother funeral. He placed second after Ian Terry. Gheesling has also made numerous stops as a special guest on Big Brother Canada

Gheesling later became a public speaker, traveling to universities around the country to talk about his views on leadership, inspired by his time on Big Brother and by his work as a coach at Michigan State University. Gheesling has published multiple self-help books, including one titled How to Get on Reality TV: How a Normal Guy Got Cast on Reality TV. According to a June 2018 ABC News report, the Michigan native also works in real estate.

Gheesling, who still frequently shares his thoughts on current Big Brother seasons via social media, got hitched in 2011. He and his wife have two children: a son, Desmond, born in 2016, and a son, Miles, born in 2018. Papa Gheesling said Big Brother changed his life for the better. "It's a cool thing I'll be able to tell my kids, but really the financial impact of winning, when I won and what I did with the money, changed my life forever," he said.

Jordan Lloyd

Jordan Lloyd took home the grand prize on Big Brother's eleventh season, but she also took home an even greater prize: she met her future husband, Jeff Schroeder. The lovebirds were very popular with audiences during their time on the show, but they weren't so adored by their fellow house guests. When the pair returned to the show for Season 14, Lloyd placed fourth.

Jordan and Jeff have remained fixtures on reality TV, placing seventh on Season 16 of The Amazing Race. Jeff kept their relationship in the spotlight by proposing to Jordan on an episode of Big Brother's 16th season, and they later appeared on Marriage Boot Camp: Reality Stars.

The pair wed in 2016 and soon welcomed their first child, son Lawson Keith. The family's second child,son Layton Sarti, was born in September 2018. Jordan frequently shares updates about her adventures as a mom on her social media pages. She and Jeff also host a YouTube channel called Jeff and Jordan TV, where they occasionally share videos about their lives.

Hayden Moss

Hayden Moss took his Brigade alliance all the way to the end of Big Brother Season 12 and wound up beating out alliance member Lane Elenburg for the $500,000 prize. Although Moss has not returned to Big Brother to date, he did make an appearance on another CBS reality show: Survivor

Moss appeared with then-girlfriend Kat Edorsson on Survivor: Blood vs. Water and was originally assigned to the struggling Tadhana tribe. Moss made bold moves on the series, forcing just the second rock drawing tiebreaker in the show's history. Unfortunately, his move backfired. Moss wound up in seventh place. He and Edorsson have since split.

Moss, who graduated from Arizona State University in 2010, founded Digital Media Inc. (formerly known as Divvie) in 2013. According to his LinkedIn profile and a CBS News report, the company's "mobile technology powers custom apps for influencers, brands, and their online communities. The vision is to revolutionize mobile video creation by making it fun and simple to collaborate, and create videos together from anywhere in the world." He also apparently works as an account executive at 2Win! Global, which helps companies "win more business."

Rachel Reilly

Rachel Reilly is one of Big Brother's more divisive winners, although even people who aren't fans of the red-headed bombshell have to admit that her "floaters, you better grab a life vest" line is rather iconic. Rachel took two tries to win Big Brother, placing ninth on Season 12, but winning it all on Season 13.

Reilly has continued to appear on reality television over the years, popping up on episodes of Celebrity Big Brother, Big Brother: Over the Top, Big Brother Canada, The Price is Right, and The Amazing Race, where she and her beloved Brendon Villegas finished third on both the 20th regular season and the second all-star season. Reilly was also a vocal supporter of her sister, Elissa, when she competed on Big Brother Season 15.

Reilly has worked as a host for shows such as Reality Relapse and Hollywood Today and acted on The Bold and the Beautiful, The Doll Web Series, and Barbee Rehab. Her film roles include the horror flick Axeman 2: Overkill, the drama Papa, the comedy Humble Pie, and thriller The Letter Red

Much of Reilly's energy has been focused on her family. She married Villegas, whom she met on her first season of Big Brother, in 2012; the ceremony was broadcast on WE TV. The pair welcomed its first child, a daughter named Adora Borealis, in 2016. 

Ian Terry

Ian Terry was still a student studying engineering at Tulane University when he took home the $500,000 prize on Big Brother's coaches season. Although he initially raised eyebrows for his strange antics in the house, Terry later became a fan favorite thanks to his sweet but strategic game.

Although he hasn't returned to the Big Brother house for another full season, Terry has returned to the show a couple times as a guest, and he has also appeared on Big Brother Canada and The Price is Right. In 2013, Terry was a contestant on Reality GameMasters, a web series in which former Big Brother and Survivor players compete in a game of Risk. In June 2018, TMZ reported that Terry would appear on The Amazing Race.

According to his LinkedIn profile, Terry graduated from Tulane in 2013. Shortly after, he landed a job as a physics teacher at YES Prep Public Schools. He was promoted to Physics Course Lead in 2017, helping physics teachers in the Houston area learn how to better teach students coming from low-income families.

Andy Herren

Andy Herren won Big Brother's controversial season Season 15, which was plagued by accusations of racism and homophobia. Herren ultimately became the first openly gay house guest to win the game.

Going into the Big Brother house, Herren had previously worked as a public speaking professor at the College of DuPage. After the controversy, the college posted a message on Facebook asserting that he did not currently work for them; Herren later clarified, saying that he had only ever been an adjunct professor, not a permanent staff member. 

Herren's Twitter bio says he is still teaching, and he's also gone into business. Having reportedly settled in Chicago, he remains active on social media – maybe too active. He got himself into a lot of hot water in July 2018 when he reportedly tweeted (and then deleted) that fellow houseguest Amanda Zuckerman had died. He also got himself roasted by Wendy's on Twitter which, if we're being honest, is definitely the dream.

Derrick Levasseur

Derrick Levasseur easily ran the game on Big Brother's 16th season, taking home the top prize seemingly without even breaking a sweat. Although some would argue that his dominating strategy made for a boring season, Levasseur certainly solidified his spot as one of the best people to ever play the game, making it all the way to the end without ever being nominated.

Levasseur was a Rhode Island police sergeant when he entered the Big Brother house, but he's now shifted his focus toward television. In 2017, he helped lead the Investigation Discovery docuseries Is O.J. Innocent? The Missing Evidence. He promoted the show with an appearance on The Dr. Oz Show. Working with his documentary partner, forensic psychologist Kris Mohandie, the duo collaborated again on the Investigation Discovery series Breaking Homicide, which tries to solve cold cases. That series, which premiered in April 2018, follows a different case each episode. 

In addition to his television work, Levasseur is married and a father of two.

Nicole Franzel

Nicole Franzel didn't make it to the end of Big Brother's 16th season, but she did endear herself to fans thanks to her quirky personality and her showmance with Hayden Voss. She eventually broke up with Voss and then returned to the show for Season 18, embarking on yet another showmance with Corey Brooks. The second time around, she took her game all the way to the end, becoming the first woman to beat out a guy in the final two.

Although her relationship with Brooks didn't last, she did find another love on the show, so maybe the third time's the charm. Victor Arroyo, apparently had a crush on Franzel during the show but didn't say anything due to the whole Brooks thing. Franzel and Arroyo got engaged in September 2018 during a visit to the infamous house, reported Entertainment Tonight, and they'll compete as a couple on Season 31 of The Amazing Race