“The Whiner Line” is a regular Big Show feature which consists of listeners calling in and leaving complaints/whines on a voicemail system, which is played at the end of the show each weekday at 5:40pm. Complaints/Whines cover a wide range of subjects, including sports teams and stars, the hosts, other listeners, celebrities, current events and local politicians. The Whiner Line is the highest rated 15 minutes of radio in Boston. The messages often include impersonations of celebrities and local figures.

There are numerous running jokes on the Whiner Line, many of which are by local comedian Graig Murphy, who performs impersonations of which include Tom Menino, Robert Kraft, Terry Francona, Grady Little, Shannon Sharpe, Harry Kalas, Deval Patrick and Dave Lewis. Other impersonators include Glenn Ordway, Mikey Adams, Johnny Damon, Carson Kressly, Bob Neumeier, Borat, Roger Clemens, Eddie Andelman, Bill Clinton, Fred Smerlas, Don Imus, Bill Walton, Edna Jacobson, Dale Arnold, and Dick Radatz as well as a caller who compiles Red Sox and Patriots-themed top-ten lists, a Beavis and Butthead parody, a caller whose comments were parody songs based on Simon & Garfunkel’s “The Boxer”, a caller known as the “Man on the Way Up” who calls regularly and insults the hosts, a caller with an Irish accent who recites poetry, and a caller known as “Mole #9″ who frequently threatens co-host Steve DeOssie with revenge for supposedly stealing $5 from him [Mole #9] in the late 1970s.

The Big Show then hosts an annual event known as “The Whiny Awards,” a tribute to the best “Whiner Line” callers of the year.