!!For the Albums:

!!For ''WesternAnimation/TheAlvinShow'':
* In the musical segment for "Down in the Valley" has Theodore giving the audience [[FlipTheBird the finger]] during the line "hear the wind blowing, hear the wind blow."
* In another musical segment, "Oh Gondeliero!" has people seen drinking alcohol.
* In "Bicycle Built for Two", Dave (a grown man) gives Daisy Belle (a girl) a bike ride all the while singing to her[[note]]he gives her a ride because the Chipmunks were distracting her so they can take turns riding her new bike... after she told them that they couldn't ride it![[/note]]. If it were present time, Dave would have been considered a [[MistakenForPedophile pedophile]].
** Plus, there's Alvin's comment at the end: [[{{Lolicon}} "Now, what does she see in him?"]]

!!For ''WesternAnimation/AlvinAndTheChipmunks''/''The Chipmunks'':
* 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 infamous "Sploosh" episode, 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 how he feels about being a SEX SYMBOL! He is unsure how to answer that directly, but suggests that his glasses may have sex appeal.
* 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, with small dots drawn on. Admittedly, such a thing back in the 80s was probably no big deal unlike today, but come on, what the hell?
** 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 again, did we mention 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.
* 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. Still...
* Depending on how you interpret it, in an early episode of the '80s series, Alvin runs for school president, and at one point, his campaign slogan is: "Don't be a donkey, vote for Alvin!"
* In the episode "Experiment in Terror", [[MistakenForPedophile Dave seems a little ''too'' excited at the sight of Brittany in her new dress]].
* 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?
* 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.

!!For ''WesternAnimation/TheChipmunkAdventure'':
* Brittany, Eleanor and Jeanette got a lot of panty shots during "The Boys and Girls of Rock and Roll!" musical segment.
* [[DirtyKid The Arabian Prince]], who's a kid if not toddler, wants Brittany [[HaremSeeker to be "one of his wives".]]
* The scene where the Chipettes 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 BellyDancer 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. Blatant VisualInnuendo, much?
* The two main villains are seen smoking or at least holding cigars throughout the film.
* While The Chipmunks and Chipettes struggle with controlling their balloons, Klaus can be heard muttering, "Gott it himmel!", which is German for, "God in Heaven!", of which can be interpreted as a swear against God, which is usually unheard of in children's entertainment.

!!For the direct-to-videos:
* In ''WesternAnimation/AlvinAndTheChipmunksMeetFrankenstein'', Alvin finds the FrankensteinsMonster (that was chasing them the night before) in Theodore's bed. Alvin goes wake up Simon and they both arm themselves with a bat. Now replace said FrankensteinsMonster with an actual man...
* Then in ''Film/LittleAlvinAndTheMiniMunks'', Dave drops toddler-aged Chipmunks and Chipettes (all six are puppets) with his friend Lalu so he can concentrate writing a song over the weekend. That means the six have to stay overnight and all the Chipmunks/Chipettes share the same bed with Lalu. Picture a babysitter sleeping with your kids...
** [[FridgeLogic Because no babysitters have sleeping bags, spare beds, or couches?]]

!!For the [[Film/AlvinAndTheChipmunks live-action/CGI films]]:
* There was a ''stripper'' reference in the second live action CGI movie, 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. It did, however, originate from strippers, so it still counts.