Sasso was born in Ladner, British Columbia, Canada. His parents are Italian immigrants. He graduated from Delta Secondary School in Delta, British Columbia in 1993. He credits his determination to become an actor and his respect for comedy to an "unhealthy addiction to television

At the age of 15 he landed his first agent and quickly began booking roles in television and film. Before moving from Vancouver to Los Angeles, California, Sasso starred for five seasons as quirky teen `Derek Wakaluk' on the award-winning Canadian dramatic series Madison.

By the end of its second season (1996–1997), MADtv experienced its first big cast turnover. Three of the show's repertory performers (Bryan Callen, Orlando Jones and Artie Lange) left the cast. As a result, in 1997, casting executives at FOX had to cast replacements for the show. Sasso (along with Alex Borstein and Aries Spears) was selected to join the MADtv third season cast as a regular cast member.

Sasso is known for quirky characters such as the accident prone handyman Paul Timberman, Eracist member Hugh, singer Michael McCloud, Talkin' American host Rui Peranio and Mexican luchador Señor Bag of Crap. Sasso also does many celebrity impersonations, including impersonations of Arnold Schwarzenegger, Chris Farley, Steven Seagal, Bill Clinton, Drew Carey, Elton John, Elvis Presley, Fred Durst, George W. Bush, James Gandolfini (as himself and Tony Soprano), James Lipton, Jesse Ventura, Kenny Rogers, Lance Bass, Louie Anderson, Paul Shaffer, Randy Newman, Richard Simmons, Robert De Niro, The Rock, Steve Austin, Wayne Newton, William Frawley (as Fred Mertz from I Love Lucy), and William Shatner (as himself and as James T. Kirk). Will began developing several network television projects with Disney/Touchstone for ABC in 2001 and in 2002, Sasso left MADtv to pursue the next stage of his career.

Sasso is a professional wrestling fan, and has made appearances with multiple American pro wrestling promotions. Sasso engaged in a worked shoot angle with former world champion wrestler Bret Hart, which began on February 6, 1999 during Hart's second guest appearance on MADtv. In a sketch lampooning the election of Jesse Ventura to gubernatorial office, Hart "broke character" and attacked the cast members for making light of wrestling, apparently injuring Sasso. He then appeared in a later episode at the curtain call during the ending credits and again attacked Sasso in an "unscripted" assault. Sasso then appeared at ringside during the February 8, 1999 episode of WCW Monday Nitro, where Hart again attacked him. Sasso retaliated by interfering in Hart's match against Roddy Piper, making him lose the match and the WCW United States Championship. This led to a grudge match on the February 15, 1999 episode of Nitro, where Sasso appeared with castmate Debra Wilson, who turned on Sasso, making it a one-sided match.

Sasso's impersonation of Steve Austin impressed the WWF (as it was then still known, before its name changed to WWE) so much that they asked him to be part of the February 7, 2002 episode of WWF SmackDown!, appearing alongside Chris Jericho and Austin himself, as a means to promote Austin's upcoming "MADtv" appearance. Sasso also appeared in the audience at WrestleMania X8, and can clearly be seen in the front row during the match between Ric Flair and The Undertaker.

On the live April 9, 2012 broadcast of WWE Raw, he appeared along with the other actors in The Three Stooges movie, alternating between Curly and Hulk Hogan impersonations. He was chokeslammed by Kane.

Since leaving MADtv, Sasso's television appearances include four seasons as Carl Monari on Less than Perfect, as well as a role in Robson Arms. Sasso also played the role of Fortunio Balducci in Southland Tales. Sasso starred in $h*! My Dad Says, based on the Twitter feed Shit My Dad Says created by Justin Halpern. The show premiered in the fall of 2010 and its cancellation was announced on May 15, 2011.

He also appeared in the 2002 Sum 41 music video "Still Waiting" as the manager for the band. Sasso hosted the 2006 Canadian Comedy Awards in London, Ontario as well as the festival's "Sketch & Improv Showcases". Additionally, he was a host at the 2005-2006 NHL award ceremony. Sasso appeared on the CSI episode "The Chick Chop Flick Shop". He also appeared on the Childrens Hospital episode "Frankfurters". As of February 20, 2012, he hosts 10 Minute Podcast with Chris D'Elia and Bryan Callen.

In 2013, he started a series of Vines where he violently "vomits" lemons under various circumstances. The clips have become very popular on the internet. Sasso will be starring in a new animated series on FOX entitled Murder Police, which will be released in July 2013.

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