After graduating, cum laude, from Williams College, Leddy moved to New York City, where he started his career at MTV Networks as a writer for VH1. He quickly became a producer, and joined sister channel MTV where he rose to Senior Producer/Writer. After overseeing studio-based shows and VJ segments, Leddy developed and created series for the network. He created the in-depth artist profile series "MTV Rockumentary," produced the pilot and first 7 episodes of "MTV Unplugged," and wrote/directed/produced MTV's "Half Hour Comedy Hour." After 7 years with MTV, Leddy went freelance and formed the production company BLIP Inc.. He continued to work with MTV, producing, writing, and directing one-hour comedy specials financed by the movie studios as promotional vehicles for their films. Several of these starred Mike Myers including the "MTV Wayne's World" and "Wayne's World II Specials," and "Austin Powers' Electric Pussycat Swinger's Club," a show styled after the psychedelic '70's comedy series Laugh In, and Playboy After Dark. He also directed comedy specials for HBO, Showtime, and Comedy Central, as well as a muppet holiday movie for Fox broadcast and Sony Home Video called CinderElmo, starring Keri Russell, Oliver Platt, Kathy Najimy, and French Stewart. During production of an MTV special promoting the Mike Myers TriStar Pictures film "So I Married an Axe Murderer," Leddy was offered the chance to direct his first feature film, a coming of age comedy called Bad With Numbers. Shot in Wilmington, North Carolina in 1994, the film starred Jason London, Tia Carrere, Jeffrey Tambor, Alexandra Lee, and Zak Orth. Two months before the film was to have a 1200 screen theatrical release, the distributing studio Savoy Pictures went bankrupt and the film was left in limbo. Eventually it was acquired by Trimark Pictures, and under the title My Teacher's Wife aired numerous times on the USA Network, and was released on DVD.
Move to Los Angeles
In 2000, Leddy moved to Los Angeles, and began a directing job at Fox's late night sketch comedy showMADtv. A two-week tryout ended up as a 9-season run, with Leddy becoming the primary director, logging over 200 episodes, and eventually becoming Co-Show Runner/Executive Producer along with head writer John Crane. Leddy continued to freelance on the MTV Movie Awards and MTV Video Music Awards. He wrote and directed the opening short film for the 1999 MTV Movie Awards, The Pitch , starring Ben Stiller, Vince Vaughn, and James Cameron. He also directed short films with Marlon Wayans and Shawn Wayans when they hosted the VMAs in 2000. In 2005, during hiatus from MADtv, Leddy directed and produced an independent film based on his original screenplay called Shut Up & Sing. The ensemble comedy/drama is about a group of guys who sang together in a college a cappella group who reunite 15 years later to sing at a friend's wedding. With the help of renowned casting directorAvy Kaufman, Leddy assembled a stellar cast of New York-based performers including Mark Feuerstein, Molly Shannon, David Harbour, Rosemarie DeWitt, Elizabeth Reaser, and Reg Rogers. The film was shot on location in New York City and East Hampton, NY. On the festival circuit, the movie won 9 awards including the Audience Award at the HBO U.S. Comedy Arts Festival in Aspen. Just prior to a limited theatrical release by Strand Releasing, the Weinstein Company announced they were naming their previously untitled Dixie Chicks documentary "". A brief legal skirmish ensued and Leddy was forced to re-title his film, first as Sing Now or Forever Hold Your Peace, and then for international sales purposes, as The Wedding Weekend, and that title proved more popular with DVD distributors where it was picked up by First Look Studios and released in May 2008 on DVD. In May 2010, the film began airing on The Sundance Channel as The Wedding Weekend. It has been seen in multiple countries in Europe and had a theatrical release in Mexico in 2009.
