• Franklin Pierce Adams (1881-1960), journalist and wit
• Alan Arkin (born 1934), actor, director, musician and singer
• Lucie Arnaz (born 1951), actress, daughter of Lucille Ball and Desi Arnaz
• George Balanchine (1904–1983), choreographer and influential figure in ballet
• Paul Cadmus (1904–1999), painter
• Frank Converse (born 1938), actor
• John Curran (1953–2013), financial journalist
• Rodney Dangerfield (1921–2004), comedian
• Bette Davis (1908–1989), actress
• Alice De Lamar (1895 – 1983)
• Sandy Dennis (1937-1992), theater and film actress
• Clifton Fadiman (1904-1999), author, editor, radio and television personality
• Jose Feliciano (born 1945), singer and songwriter
• Leopold Godowsky (1900-1983), noted violinist, chemist, and co-creator of Kodachrome
• Seth Grahame-Smith (born 1976), author, film and television producer, grew up in town
• Ann Harding (1902-1981), film, radio and television actress
• John Marshall Harlan II (1899–1971), Associate Justice of the Supreme Court, summered in Weston, buried in Weston's Emmanuel churchyard
• Mariette Hartley (born 1940), actress, native of Weston
• June Havoc (1912-2010), actress, dancer, writer, theater director and younger sister of Gypsy Rose Lee
• Evan Hunter (1926–2005), author who wrote under the pen name "Ed McBain"
• Erica Jong (born 1942), author
• Eartha Kitt (1927–2008), entertainer, moved to town in 2002
• Lawrence Langner (1890–1962), playwright, author, and producer. Lived on what is now called Langner Lane
• Ring Lardner (1885-1933), sports columnist and short story writer
• Eva Le Gallienne (1899–1991), actress
• Sinclair Lewis (1885-1951), novelist, writer and playwright
• Paul Michael Levesque (born 1969), "Triple H", wrestler, World Wrestling Entertainment
• Stanley Matthews, former Wimbledon Boys' Champion and son of Sir Stanley Matthews
• James Melton (1904-1961), singer, antique car collector
• Marilyn Monroe (1926-1962), actress, lived on Fanton Hill in 1955 after completing the Seven Year Itch
• Brent Musburger (born 1939), sportscaster
• James Naughton (born 1945), actor
• Katharine Ordway (1899–1979), 3M heiress, philanthropist, supporter of land conservation, funded the purchase of part of Devil's Den
• Walter Pidgeon (1897-1984), motion picture actor
• Jacob Pitts (born 1979), actor
• Christopher Plummer (1929-2021), actor
• Paul Rand (1914–1996), graphic designer
• Harry Reasoner (1923-1991), journalist and a founder of the 60 Minutes program
• Robert Redford (born 1936), actor, had a home in town
• Fritz Reiner (1888–1963), conductor of the New York Philharmonic, the Metropolitan Opera, and other notable orchestras. Lived on Davis Hill beginning in 1938
• Jamey Richard (born 1984), pro football player
• Keith Richards (born 1943), musician, member of The Rolling Stones
• Mort Schindel (1918-2016), an American educator and producer, the founder of Weston Woods Studios
• John Seigenthaler, Jr. (born 1955), former NBC News weekend anchor
• Donna Summer (1948-2012), singer and songwriter
• James Thurber (1894–1961), writer
• John Orr Young (1886-1976), advertising executive and co-founder of Young & Rubicam Advertising Agency

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