- Crosses the Line Twice:
- "Poisoning Pigeons in the Park":"We'll murder them all amid laughter and merriment, except for the few we take home to experiment!"
- Another pair of examples is "The Old Dope Peddler", which was so over the top when it was written that people nearly died of laughter, but when performed to modern audiences, the laughter just . . . dies away by the end because it's too topical, and "The Masochism Tango", which is so over the top it still crosses the line in the day and age of the Obligatory Bondage Song.
- And "We Will All Go Together When We Go", which was about a nuclear holocaust."Just sing out a Te Deum/When you see that ICBM/And the party will be 'come as you are'!"
- At least half his songs qualify for this trope - and they don't cross the line twice so much as dance back & forth over the line, to the sound of a catchy little piano ditty.
- Special mention must surely go to "I Got It from Agnes", which opens with the simple premise that an STD is working its way around his group of friends and they're happy with this. Then, as it lists who got it from whom, you notice around the second verse that some of his friends are clearly gay - a little controversial for its day, but nothing major. Then it mentions Pierre, who got it from François and Jacques. And Edith who got it from her father. And Daniel, whose spaniel has it now. And then it reveals that their dentist even got it and they're still wondering how.
- This one manages to use this trope while still Getting Crap Past the Radar by never actually stating what "it" is that everyone is getting from one another. The listener's mind does all the work.
- "Poisoning Pigeons in the Park":
- Hilarious in Hindsight:
- His 1960s song "George Murphy", about a senator with a former showbiz career, gets a cheap laugh from the less-than-impressive career of another politician with similar background...Ronald Reagan.
- In "Smut," he sings:
- Decades later, Alan Moore wrote Lost Girls, a pornographic graphic novel starring, among others, Wendy Darling and Dorothy Gale.
- He also played Harsher in Hindsight for a laugh, more recently saying this of "When You Are Old and Grey":Lehrer: I must confess, I wrote that song when I was 21 years old and it doesn't seem quite so funny anymore...
- In "New Math", he points out that the titular education reform was meant to help kids understand what they're doing during calculations, even as it leaves parents confused and unable to help their kids. While New Math was mostly abandoned, the subtraction method he demonstrates in the song actually stuck around. Fast-forward to the mid-2010's, and the Common Core curriculum is going down the exact same route, including new ways to learn subtraction because the "old" way (read: New Math way) doesn't teach kids what they're doing.
- With certain Vatican Issues in the news, variations on the line about kindly Parson Brown in "My Home Town" take on an eerie perspective:"I think I'd better leave this line out, just to be on the safe side."
- On An Evening Wasted With Tom Lehrer, he describes his friend who spelled his name Hen3ry.note In other words, he was the first L33t Speaker!
- Pollution's line "Now you can breathe as long as you don't inhale." got much funnier during the Clinton years.
- His self-introduction in Tom Lehrer Revisited mentions that he's "currently working on a musical comedy based on the life of Adolf Hitler", 8 years before The Producers and "Springtime for Hitler".
- Harsher in Hindsight: somehow Played for Laughs; see Hilarious in Hindsight.
- Memetic Mutation:
- YTMND seems to like putting together "The Elements"/"New Math" together with a clip of Stan talking.
- Making up new verses for the "L-Y" song. For example, this YouTube gem:You're on a Thailand tripWhen your girlfriend's panties ripHow do you bail when you notice she's a guy?Tactfully...Tactfully...Tactful...L-Y!
You're playing a Dark Souls game
- Or this one:
And you're trying to link the flame
If you can't git gud then how are you going to die?
- "Seinfeld" Is Unfunny: By 1960s standards, his work was some of the funniest, most obscene material written. Today, it's fairly tame. (Although see below, above, everywhere in between, and every other Tom Lehrer page.)
- Squick: It is a considerable credit to his songwriting talents that even after nearly half a century and all the moral decay that entails, the Black Comedy of some of his lyrics can still turn a few heads.
- Suspiciously Similar Song: "That's Mathematics" was originally written to the tune of "That's Entertainment", but he couldn't get the rights so he had to write a new tune (which is still similar because it had to fit the existing lyrics).
YMMV / Tom Lehrer