At this point, one of the most talked-about legendary, oddball crossovers in the modern history of TV was between Community and Cougar Town. Abed’s obsession with the Courtney Cox series led to actors and characters from each show appearing on the other in their respective second seasons. But these weren’t the only times they crossed over, with the second one involving the actor who played Bobby Cobb.
In Cougar Town, Bobby was the ex-husband of the main character Jules Cobb. While they maintained a strong friendship after their separation, Jules tried to rebuild her life after their marriage came to an end. The series left the concept of Jules being a supposed “cougar” behind partway through the first season, and the focus moved to a group of friends mostly living in the same cul-de-sac.
Bobby Cobb was played by Brian Van Holt through Cougar Town‘s first five seasons. He appeared in the first couple of episodes of Season 6 but left the series after that. However, Bobby returned for the show’s finale. That’s where things got odd as he wasn’t physically in the finale. Bobby FaceTimed from his new home on a tablet that Andy Torres primarily carried around throughout the episode.
To make things even stranger, Brian Van Holt also similarly appeared on Community. Season 6 dropped on the now-defunct streaming service Yahoo! Screen. While it was a comedic return to form for the series, it was missing several key characters who had moved on to other projects.
In Season 6, Episode 5, Greendale joined an experimental program that enabled prisoners to attend school via FaceTime. Tablets connected to poles on remote control cars allowed the convicted criminals to move around the campus and go to class without actually being there. It seemed like a reasonably good idea until Jeff Winger met an inmate named Willy who challenged his place of prominence at Greendale and in the Dean’s heart.
Willy was played by Brian Van Holt, making him at least the third member of the Cougar Town cast to appear on Community. What makes this even weirder is the fact that Van Holt’s final Cougar Town appearance and his only Community appearance were both as a character interacting with the cast via FaceTime on a tablet. If it were any other creator than Dan Harmon, it would be easy to write this one off as a coincidence.
It’s entirely possible that Van Holt’s Community appearance was meant as an intentional callback to his final moments on Cougar Town. Honestly, it’s hard to say how many people would have watched Cougar Town‘s final episodes on TBS and Community‘s last season on Yahoo! Screen. But in a world of streaming where everything is accessible, it’s much easier to make these connections between two seemingly disparate series.
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