Matthew Perry Guest-Starred On Two Episodes Of Michael Landon's Hit '80s Fantasy Show

Matthew Perry appeared in and starred in a wide variety of projects outside of "Friends" — including Michael Landon's hit '80s fantasy drama. We're referring to "Highway to Heaven" (which is currently streaming for free). It centered on an angel named Jonathan Smith (Landon), tasked with spreading goodwill and hope to humans on Earth as part of his probation. The series, which was created by Landon, ran from 1984 to 1989, and Perry appeared late in its run.

The rising star appeared in two 1988 episodes titled "Hello and Farewell: Part 1" and "Hello and Farewell: Part 2." They center on a teenager who, on the brink of becoming a pilot, learns that a female veteran with PTSD is his biological mother. Perry played David Hastings, the teenager. Both episodes fared moderately well with IMDb users, who graded the episodes a 7.8/10 and 7.7/10, respectively. The episodes can be watched today on various streaming sites, such as Tubi and Prime Video.

Matthew Perry was an excellent comedic and dramatic actor who was best known for playing the witty, sarcastic Chandler Bing. However, he also dabbled in a few fantasy roles outside of "Highway to Heaven." One of the earliest of his career was a Fox fantasy comedy series called "Second Chance," and later renamed to "Boys Will Be Boys." It followed a dead man (Kiel Martin) who returned to Earth to guide a younger version of himself (Perry) onto a better path. However, the supernatural angle only lasted for half of the season. The second half of the season was revamped to focus on Perry's character and two of his acquaintances, and was when the show changed titles.

Unlike some of Perry's more popular projects, the Fox series didn't have much staying power, but it remains a part of his journey. Billy Gallo, who appeared on the series with Perry as Francis Lottabucci, spoke in the new three-part Netflix documentary about Perry, which premiered on October 27, 2026. "Told through intimate testimonies from close family and friends, this documentary event reveals the real Matthew Perry — generous, funny, vulnerable, larger than life — and the battles he fought to become the man behind the icon," reads the logline (via Gold Derby). "A raw record of a life lived in full, and the honesty that became his greatest legacy."