!!For the Albums:
* In ''A Very Merry Chipmunk'', Alvin decides to give up the harmonica for the saxophone, and receives pointers from Music/KennyG. Alvin then asks him "Now, do I suck or blow?" Simon responds with [[DeadpanSnarker "You definitely suck."]]
* In ''Club Chipmunk: The Dance Mixes'', Alvin covers "I'm Too Sexy". That alone should be enough, but there's even a line with him moaning about how [[{{Unmentionables}} he loves]] [[AdvertisingCampaigns his Calvins]].

!!For ''WesternAnimation/TheAlvinShow'':
* Inadvertently funny if you live in the UK or a few other places: Alvin flicks a very clear “inverted” VSign while gesticulating in “Alvin For President”.
* In another musical segment, "Oh Gondeliero!" has people seen drinking alcohol.

!!For ''WesternAnimation/AlvinAndTheChipmunks''/''The Chipmunks'':
* In general there seem to be a lot of {{Panty Shot}}s (from the Chipettes and other young girls) for no reason, although that may be an attempt at realism, as some of their skirts are quite short.
* In "Romancing Miss Stone", during the scene where Alvin and Dave are duelling over the hand of Alvin's teacher, Alvin yells out "Take that, you gigolo!" as he hurls a water balloon at Dave.
* In the episode "Sploosh", Brittany's character at one point asks Jeanette (as the mermaid), "Are mermen sexier than human men?"
* Even better from "Simon Seville, Superstar", Simon (an eight-year-old boy chipmunk) is asked if he considers himself a sex symbol (Bonus, Alvin does a more-or-less simultaneous and very loud gasp with the word "sex", just to confirm this trope). He demurs cutely and says "No... Only if glasses are sexy". When told that they ''are'' SexySpectacles (or "very attractive", at least), he pulls out ones that are older and even more noticeable.
* In "Cinderella? Cinderella!", where Brittany dreams herself in the role of Cinderella, a scene of her forced to do various chores has her giving baths to her sisters. Both Jeanette and Eleanor's expies in the dream are shown sitting in small bathtubs, uncovered from the waist up. Possible only because they are {{Fully Dressed Cartoon Animal}}s, obviously.
** Also, depending on what The Chipettes are wearing, it seems like the animators like to draw them with busts from time to time, despite them being eight-years-old. Most notably, in the episode "Staying Afloat", bikini-clad Brittany constantly goes back and forth between being flat-chested, and having breasts.
*** In a storybook adaptation of the episode, "The Greatest Show-Offs on Earth," an entire page has The Chipettes doing their acrobatic number, drawn with both breasts ''and'' HartmanHips... and they're only eight years old.
* "Dreamlighting", which parodied the show ''Series/{{Moonlighting}}'', has what appears to be a distraught Alvin suffering a hangover. Then we see that he's just been drinking ''root'' beer and he's had far too much.
* Alvin sees a psychiatrist in the episode "Alvin and the Analyst", who supposedly is a caricature/parody of a real-life ''sex'' therapist; granted, Alvin wasn't seeing the shrink for ''those'' kinds of problems, but still parodying a sex therapist on a kids' show is weird.
* The entire "Proud Mary" number from the episode "Goin' Down to Dixie" so much that it actually spawned an ''entire article'' based on a troll's [=YouTube=] comment that The Chipettes are, "A pedophilic rape waiting to happen", on the grounds that their New Orleans-inspired dresses were inappropriate for girls their age, while others argued that not only did the dresses fit the number they were performing, but they're ''chipmunks'', not little human girls. In short, The Chipettes' performance of "Proud Mary" is almost as controversial today as their "Gettin' Lucky" number from ''WesternAnimation/TheChipmunkAdventure'' had become.
** Since they're wearing 19th-century showgirl dresses and stockings, the girls are very covered up, much more so than modern pop standards. Their foster mother is also sitting in the front row and clapping along. This one's gotten blown way out of proportion, to say the least.
* In the "Bigger" episode of ''Chipmunks Go To The Movies'', Alvin and company wear shirts with their band name on it. "Fur Balls". (Even when Alvin's much older.) It's almost enough for a SpitTake if you're watching as an adult.
** When the record producer calls to dismiss Alvin from his job, the audio as it stands in the current print is "Hey, take all the time you want! We just saw your video: you're fired!", at the end of which there seems to be a bump in the animation. This troper recalls watching the episode on TV and hearing him say "It sucked!" after "your video". It appears that the line was bowdlerized. Could anyone confirm that it was originally there?

!!For ''WesternAnimation/TheChipmunkAdventure'':
* Brittany, Eleanor and Jeanette got a lot of panty shots in the movie, especially during "The Boys and Girls of Rock and Roll!" musical segment.
** Brittany also does a SexyWalk and generally shakes her hips a lot.
* [[DirtyKid The Arabian Prince]], who's a kid if not toddler, wants Brittany [[HaremSeeker to be "one of his wives".]]
* The scene where Brittany and Jeanette have to get past a swarm of snakes. How do they do that? By charming them, of course. How do they charm them? By singing. (While wearing BedlahBabe outfits, too) And the name of the song they sing? "[[IntercourseWithYou Getting Lucky]]". No more need be said.
** And the snakes '''go rigid''' when they're actually charmed. Maybe a blatant VisualInnuendo but, to be fair, that is actually the normal position for cobras who are either preparing to attack or are being charmed.
* The fiesta the boys take part in in Mexico City might actually be worse than the now-semi-infamous "Getting Lucky", and a case of DoubleStandard -- the human women they dance with are wearing very low-cut blouses, the Carmen Miranda number they perform has Alvin getting full-on smooched after asking a little girl whether she likes his hips, and "Cuanto le gusta" is Spanish for "she really likes it!"
* The two main villains are seen [[GoodSmokingEvilSmoking smoking or at least holding cigars throughout the film]]. This is a ValuesDissonance, as there was absolutely no issue with having smoking in a children's movie in the late 80s.
* While The Chipmunks and Chipettes struggle with controlling their balloons, Klaus can be heard muttering, "Gott in himmel!", which is German for, "God in Heaven!", which can be interpreted as profanity, which is usually unheard of in children's entertainment.

!!For the [[Film/AlvinAndTheChipmunks live-action/CGI films]]:
* There was a ''stripper'' reference in the ''Squeakquel'', however, since they didn't say "stripper" or "prostitution" outright, [[ParentalBonus most of the kids in the audience won't get it,]] which is what makes this a GettingCrapPastTheRadar... or past the kids, anyways:
-->'''Alvin:''' It's Aunt Jackie. She's making us a zesty five-course meal.\\
'''Dave:''' Really? Well, can I talk to her?\\
'''Theodore:''' She's practicing her pole dancing.\\
(''Alvin and Simon look at each other'')\\
'''Dave:''' ''Pole dancing?''
** Learning/practicing pole dancing has recently become a well known workout, however, so it might have been just that. (Aunt Jackie was also in a wheelchair, which might explain Dave's surprise.) It did, however, originate from strippers, so it still counts.
** For that matter, in the first movie, Simon mentions the very-short-skirted and attractive housekeeper "Uncle Ian" sent over is also a [[HappyEndingMassage masseuse]].
* In ''Chipwrecked'' Alvin swings right into a tree moaning "Ow! [[GroinAttack My acorns!]]"
* Also in ''Chipwrecked'', from Ian, who mentions that "one time [[Music/SnoopDogg Snoop]] started [[TheStoner a blaze]] just using two carrot sticks!"
* In ''Road Chip'', Miles tells the Chipmunks that Dave will leave them in the forest holding their nuts.
** The entire scene involving Creator/JohnWaters' cameo, with Alvin namedropping ''Film/PinkFlamingos'', which he has apparently seen.
** The "Uptown Munk" number plays with this one in all sorts of ways, by bowdlerizing the alcohol mention, in a scene where alcohol is both consumed and mentioned (granted, by someone of legal drinking age), and by leaving in the cocaine reference.
* Also in ''Road Chip'', Theodore raps the beginning of [[Music/SirMixALot "Baby Got Back"]] straight off, up to and including the ''"get sprung"'' part.

!!For ''ALVINNN! and the Chipmunks'':
* The episode "Knights" involved a group and song called the Knights of Boogie. A lot of [[Film/BoogieNights "Boogie Knights"]] were mentioned.