1. This is the city that Willy Loman said he would go to as his career dissolved in Arthur Miller's Death of a Salesman.
2. In A Connecticut Yankee in King Arthur's Court, Hank Morgan explains he was born and raised in this city, or "anyway just over the river."
3. This is where Sydney Ellen Wade (Annette Benning) decided to move "to run Reynold's campaign" after being fired from her environmental lobbying job while dating President Andrew Shepherd (Michael Douglas) in the film The American President.
4. Homer Simpson and family thought they won a trip to Hawaii, but they actually won a trip here.
5. In the World War 2 film Kiss Them Once for Me starring Cary Grant, sailor Ray Walston makes a person-to-person call to his wife who works at Pratt & Whitney and lives in this city.
6. On the television show Mad About You, Jamie Buchman (Helen Hunt) tells her astrologer she was born in this city on February 19, 1963 at 4:30 am.
7. Adam Sandler, in the Saturday Night Live skit "Where You Headed?" answers that there are fourteen Dunkin' Donuts between Sturbridge and here.
8. On Who Wants to be a Millionaire? five percent of the audience picked this place as the answer to the question "In what American
city would you find Fanueil Hall?"
9. On the game show Twenty-One, the answer is "False" when a contestant is asked if the New England Patriots are located here.
10. In the West Wing episode 'Let Bartlet be Bartlet," presidential advisor Toby Ziegler's office has a framed copy of a newspaper
from this city.
11. It's a Trinity College student located in this city who reports the very first shark victim in the movie Jaws.
12. Garrison Keillor's character Guy Noir catches a flight here to search for a missing Renoir painting.
13. In The Contender, President Jackson Evans (Jeff Bridges) suggests that Senator Sheldon Runyon (Gary Oldman) opposes his choice for vice president because Evans embarrassed Runyon
during a debate hosted in this city.
14. Al Franken spent 144 days as President of the United States (as recorded in his book Why Not Me?). This city is host to the Al Franken Presidential Library.
15. In the 1946 movie The Stranger, set shortly after World War 2, a Nazi hunter named Wilson (Edward G. Robinson) tracks down the infamous Franz Kindler (Orson Welles) who is posing as a professor in this "sleepy college town."
16. In the 1956 movie "Rock Around the Clock" with Bill Haley and
the Comets, the evil music promoter Corrine Talbot books Bill and
the boys at the 'Mansfield School for Girls' to perform at a high
school prom in this city.
17. Tom Magliozzi of NPR's Car Talk called it "an evil place" and
then complained that despite all his insults, this city's mayor still
hasn't called to complain.
18. West Wing's Congressman Matt Santos (Jimmy Smits) secretly flew himself back from this city to orchestrate a vote against the Republican majority.
19. Kenny's Restaurant (now Red Rock) in this city is frequently a local site seen in the television court drama Judging Amy.
20. In the 1947 fact-based film Boomerang, Bridgeport newsman Sam Levene helps State's Attorney Dana Andrews solve the murder of a beloved priest when he takes a last-minute trip north to this city and discovers a shady real-estate deal involving banker Ed Begley.
