In 1994, Buckley and his collaborator Frank Todaro were offered the chance to direct a few unscripted, very low-budget promos for ESPN's hockey telecasts.

[4] Over its 25-year run, the campaign has featured appearances from several sports stars, including Kobe Bryant, Wayne Gretzky, David Ortiz, LeBron James, Mike Tyson, and Michael Phelps.

[2] In 1997, Buckley co-founded Hungry Man Productions along with "This is SportsCenter" creator Hank Perlman and long-time producer Steve Orent.

However, the Monster.com ad continued to get airplay over the next few days while conversation around other commercials died down, and the job site ended up crashing due to increased user activity.

Hungry Man has offices in New York, Los Angeles, London, Rio and São Paulo, and has a slate of directors including Taika Waititi, Wayne McClammy, and Nanette Burstein.

The ad features a chimpanzee, wearing an oversized E*Trade t-shirt, flanked by a pair of men in a disheveled two-car garage, all facing the camera.

The campaign, titled "Rivalry", had actors John Krasinski and Alec Baldwin engaged in trash talk as fans of their respective teams, the Boston Red Sox and New York Yankees.

[12] The spot, which stars John Krasinski, Chris Evans, Rachel Dratch, and David Ortiz features the Massachusetts natives over-enunciating the distinctive vowels of the classic Boston accent as they talked about Hyundai's new Sonata.

[14] Buckley directed the NFL’s 2023 Super Bowl spot, Run With It, starring Diana Flores — the Mexico Women’s National Flag Football quarterback.

It features sports icons and athletes alike: Erin Andrews, Billie Jean King, Vanita Krouch, Bella Rasmussen, Cam Heyward, Jalen Ramsey, Davante Adams, Aidan Hutchinson and Sauce Gardener.

Run With It won a gold Clio, finished second place on USA TODAY’s Ad Meter[15] and it’s excellence was further recognized with a Sports Emmy win.

The film, set in 2008, is about rookie Canadian journalist Jay Bahadur's plan to embed himself among the pirates of Somalia to provide a close-up look at who they are, how they live, and the forces that drive them.

[25] Buckley also took the Titanium Lion and the top honors, a Grand Clio for his Microsoft "Changing the Game" work showcasing Xbox's new adaptive controller, the first ever system designed to be inclusive of handicapped gamers.

[26] Buckley's second Academy Award nomination for Short Film within the same decade is the first time a director has managed to return to the category in over 30 years.

Congressmen Adriano Espaillat and Vicente Gonzalez stated the film "amplifies global awareness" of the issue, and demanded justice for the victims and an investigation into the whereabouts of the remaining survivors.

On June 4, 2021, Buckley partnered with ad agency Leo Burnett and two parents of a child killed in the 2018 shooting at Marjory Stoneman Douglas High School to mislead gun rights activists John Lott and David Keene into believing they were to give a dress rehearsal for a 2021 graduation address for a fictitious school called the "James Madison Academy".

[29] On October 26, 2024, at 9:00am ET, Buckley launched TrumpCellCam.com, which featured a satirical 24/7 "livestream" video of former president Donald Trump's would-be life in a prison cell.

The website also encouraged viewers to register to vote and educated them on the election, detailing the candidates' respective stances on critical issues and all of Trump's ongoing criminal trials.