The Whiffenpoofs have performed for generations at a number of venues, including Lincoln Center, the White House, the Salt Lake Tabernacle, Oakland Coliseum, Carnegie Hall and the Rose Bowl.

[8] In early February 2018, the Whiffenpoofs announced (in a joint statement with their sister group Whim 'n Rhythm) that students of all genders would be eligible to audition.

For the lyrics, Yale students Meade Minnigerode and George S. Pomeroy[1][13] adapted Rudyard Kipling's poem "Gentlemen-Rankers".

The chorus, as sung by flyers and crews of the U.S. Army Air Forces' daylight bombing effort during World War II, played a key role in the 1949 movie 12 O'Clock High.

It is heard first in the background when Harvey Stovall (Dean Jagger) surveys the abandoned Archbury airfield in 1949, just before his flashback to 1942 begins.

The men sing it quietly in the Officer's Club after the unit receives its first commendation, baffling Stovall and General Savage (Gregory Peck) with their subdued reaction: "They aren't celebrating the way kids ought to…" At the end of the film, when Stovall returns to the present, the refrain of "Don't Sit Under the Apple Tree" shifts with a flourish of trumpets to the remembered voices singing "We're poor little lambs..." which becomes a triumphant instrumental phrase and fanfare over "The End."

In the 1952 comedy film Monkey Business, the tune comes on the radio and Cary Grant starts singing it to Marilyn Monroe, who declares it "a silly song".

The melody is the opening theme of the 1975 television series Baa Baa Black Sheep, a fictionalization of the World War II wartime exploits of the United States Marine Corps Marine Fighter Squadron VMF-214, ancestor of the Corps's present-day VMA-214 "Black Sheep" Squadron.

The Whiffenpoofs can be heard singing in the background in the 2006 movie The Good Shepherd, in the scene where Matt Damon's character can be seen looking at the pictures in the Skull and Bones tomb after his recruitment and when his son tells him he wants to join the CIA.

In the play Serenading Louie by Lanford Wilson, performed at the Donmar Warehouse in London in 2010, the song is sung by the cast and by Bing Crosby.

In The Simpsons episode "The Caper Chase", the Whiffenpoofs perform the song to Montgomery Burns, who offers the college a new library if he will have them killed.

Lehrer, an instructor at Yale's traditional rival Harvard University, sings of "glasses raised on high" (at which point he removes his eyeglasses and holds them up) and of drinking a toast "to those we love the best", to rhyme with "we'll pass [which may mean 'pass the final exams' or 'die'] and be forgotten with the rest."

Titled "The Hundred-Proofs Song", it suggested that rich students forgot about their studies and resorted to getting drunk at the bar, "...earning the grades we deserve, we know; – F – F – F!"

Depicting a heraldic wyvern with mint leaves for wings, a horse's neck, and a swizzle stick for a perch,[citation needed] it was designed by a cartoonist from campus humor magazine The Yale Record.