If you’ve ever listened to “This American Life” — the quirky, insightful, thought-provoking, loosely themed hour-long radio show/podcast/cult classic that explores the oddest corners of human nature — you’ve no doubt wondered: “Who are these people? Where do they come from?”
For 2 consecutive weeks this month, this answer was: Westport.
First up was a story by writer Rosie Schaap. According to Westport Patch, in 1986 — at age 15 — she got on Metro-North in Westport and “discovered the bar car.” It was “a dingy, crowded, badly ventilated chamber where commuters drank enough to get a decent buzz going, told dirty jokes and chain smoked.”
They were, Rosie says, “my kind of people.”
She quickly learned to read tarot cards for riders. In exchange, they bought her beers. It was a great life, until one day…

Marilyn Monroe
Just a week later, This American Life told the tale of John Reznikoff. The owner of Westport-based University Archives — a buyer and seller of rare documents, manuscripts and Barack Obama’s old Jeep Grand Cherokee — stumbled across documents linking 3 American icons: President Kennedy, Marilyn Monroe and the mob. The story took an interesting turn when the material turned out to be forged — by Reznikoff’s best friend.
(In that weird, 6-degrees way of the world, back in the day Marilyn Monroe was one of Westport’s most famous summer residents.)
A half century ago, Rod Serling produced amazing stories for TV’s “Twilight Zone” — some of which were written in, or described, the Westport where he lived.
Today Ira Glass presents a different, but equally compelling, series of tales on radio. For 2 straight weeks, they’ve had a Westport connection.
DEE-DEE dee-dee DEE-DEE dee-dee…
(To hear Rosie Schaap’s story on This American Life, click here. For John Reznikoff’s episode, click here.
