Matt Damon and Ben Affleck Humorously Tackle Berkshire Town Names on Tonight Show

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Matt Damon and Ben Affleck Humorously Tackle Berkshire Town Names on Tonight Show

Film stars Matt Damon and Ben Affleck recently took to the stage on “The Tonight Show Starring Jimmy Fallon” to humorously tackle the challenge of pronouncing the names of every city and town in the Berkshires. This entertaining segment featured the trio, styled as “Three Guys from Boston,” showcasing their Bostonian charm and accent.

Berkshire Cities and Towns Challenge

During the Tuesday evening segment, Damon, Affleck, and Fallon recited a total of 351 municipalities in Massachusetts. They presented the names in alphabetical order, embracing exaggerated Boston accents and winter attire that represented their hometown pride.

Highlights of the Segment

  • The trio named 32 cities and towns located in Berkshire County, ranging from Adams to Windsor.
  • Affleck expressed surprise over the existence of a town named “Peru,” humorously questioning, “Peru, really?”
  • Fallon finished the list with “Windsor,” the final town on the Berkshire roster, while also identifying Pittsfield as the county’s most populous city.
  • Damon impressively pronounced “Tyringham,” while Affleck skillfully dropped the “R” in “Alford.”

Despite their comedic delivery, the skit wasn’t without its flaws. Observant viewers noted that “Sandisfield” appeared to be dubbed in post-production due to a missed mention during the live taping. This slip may have surprised local residents, but it added to the humor of the evening.

With their characteristic playful banter and lighthearted commentary, Damon and Affleck effectively captured the spirit of their Boston roots, making for a memorable segment on “The Tonight Show.” This fun interaction not only entertained fans but also shed light on the unique town names found in the Berkshires.