On Big Brother All-Stars (US), Will entered the house with a huge target on his back due to being the only winner in the game. However, with the help of fellow Big Brother 2 housemate and "Chilltown" member Mike "Boogie", Will was able to manipulate other houseguests (most notably his new showmance parter Janelle Pierzina) and managed to get rid of big names like Howie Gordon, James Rhine, and Danielle Reyes just to name a few. Will's ultimate demise was during the final 4 when Erika Landin and Janelle caught onto Chilltown's schemes. Since Mike "Boogie" was the HOH of that week and could not be evicted, Janelle, the Power of Veto holder of that week, casted the sole vote to evict Will from the house, making him the 6th member of the jury. At the finale, Will voted for his ally Mike "Boogie" to win the game.
The Big Brother 2 Final HOH competition was point based as opposed to the normal format. Will won Part 1 with 5 points, but placed last in Part 2 with 5 points once again. His cumulative total of 10 points allowed him to finish in second overall and qualified him to compete in Part 3.
Due to the COVID-19 Pandemic, Will could not host the roundtable for Big Brother 22 or Big Brother 23. Instead of hosting the roundtable for BB22, Will moved into the "next-door neighbor's house" to host Neighbor's Week for the All-Stars, tempting them with power and prizes. He did not appear in BB23 in any form.
Will competed on the Big Brother Primetime Special of The Price is Right that aired on May 24, 2016. At the end of the episode, it was revealed that Will was declared the winner. He donated his winnings of $51,030 to charity.
Dr. Will created the term "Showmance" which is now widely used in reality programing.
Despite being recognized as the best Big Brother player in history, Dr. Will has never won a single competition. This is cited as part of his strategy as he has stated that Big Brother is based on psychological strategy and not winning "meaningless" competitions.
Dr. Will saved Ophelia, the pot belly pig, from drowning in the BB2 pool.
CBS released the results of the contestants IQ score but retracted them when Will threatened legal action. Before the retraction it was reported that his IQ was 130.
Survivor contestant Rob Cesternino claims he based his game on Will's.
Will and Danielle Reyes are the first houseguests to both reach and surpass 100 days in the Big Brother house.