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Description
I started with Ludwig and Kooky and it just grew from there...

Personally, I find the cartoon Koopalings very interesting. I've seen a bunch of episodes at this point and, as I watch more and more, these incarnations of the "Koopa Kids" more and more interesting.
So, that's when headcanons began to emerge.
HEADCANON TIME: I believe that the Koopalings, as shown in the DiC cartoons, are completely different entities from their Nintendo counterparts. They also sport distinctive personalities from their counterparts.

KOOKY (age 11), as far as his Nintendo counterpart goes, acts a lot more like Iggy than he does his own counterpart, Ludwig. While Ludwig is cool and level-headed, Kooky is pretty much insane and crazy. Ludwig doesn't take a lot of nonsense, while Kooky IS a lot of nonsense. As far as personalities are concerned, Ludwig and Kooky are complete opposites. The only thing the two really share is a certain quirk for inventing, though Ludwig isn't nearly as proficient as Kooky in this area.

KOOTIE PIE (age 16) is much more bratty than Wendy is. Wendy is also much more calm than Kootie Pie. Also, unlike Kootie Pie, Wendy can admit her own flaws. Kootie Pie's temper is much more unstable than Wendy's, but Kootie Pie's personality is also much stronger. Kootie Pie is bossier and more prideful than Wendy as well. The one thing Wendy has going for her, though, is that she's more graceful and sweeter than Kootie Pie. While Kootie Pie relies on her overwhelming personality and temper to get what she wants, Wendy goes about things in a much more underhanded way, which sometimes works out much better in the long run.

CHEATSY (age 13) is a calmer personality than rash Larry Koopa. While both rely on deception to get the job done, Cheatsy is much better at it. While Larry is mostly a small-time con artist, Cheatsy has enough finesse to make deals on the Black Market itself if he felt so led. Comparatively, Larry's like a sleazy street vendor while Cheatsy's Al Capone. Larry, though, can wrench at peoples' sympathies in a way Cheatsy can't seem to master. Since Larry's never gotten all that far, though, it's safe to say that Cheatsy's the King of Con for now.

BIG MOUTH (age 10), when compared with Morton, is much more sharp-tongued than his counterpart. Big Mouth will say what hurts. While Morton rattles off whatever comes to his head, Big Mouth is more calculative and aims for the heart with every word. Get into a fight with Morton and he's bound to forgive you within a couple of hours. Get into a fight with Big Mouth, though, and he'll be sure to make you cry.

HIP (age 6) is sweet and cute, much like Lemmy. Lemmy, though, unlike Hip, is a bit insane. Lemmy's emotional states are also a bit unstable, flying from one emotion into another if he's instigated. Hip, though, is much more innocent than his counterpart. Hip isn't angered easily and it takes a lot to get him mad (and even more to keep him that way for longer than a minute). Lemmy also isn't angered easily, but, once he's angered, he tends to stay that way for longer. Hip also is less mature than Lemmy (because, yes, that's possible) and doesn't really understand a lot about the world around him.

HOP (age 6) is pretty much nothing like his counterpart, Iggy. For one thing, Iggy is completely insane. Hop is a lot like Hip, but more timid, much unlike Iggy. Hop and Hip are as close as close can be and they can't stand being away from each other for too long. Hop also shares a curiousity of the world around him, like his twin brother. Being more timid, though, Hop tends to let Hip take the lead. While Iggy and Lemmy act pretty much independently, Hop and Hip pretty much never do.

BULLY (age 17) and Roy, on first glance, seem to share a lot of personality traits. Upon closer inspection, though, one will find that Bully is a much more calm and calculative personality than his counterpart. While Roy likes to take control, Bully likes to watch things unfold and jump in when he feels the time is best for him to do so. Roy is much hastier than Bully, not staying still for long. Roy is more overt about his actions while Bully is more underhanded. Bully likes to take things in stride and let things happen as they happen, making him a much more effective tactician.

Koopalings (left column) (c) Nintendo
Koopalings (right column) (c) Nintendo and DiC

Description
I started with Ludwig and Kooky and it just grew from there...

Personally, I find the cartoon Koopalings very interesting. I've seen a bunch of episodes at this point and, as I watch more and more, these incarnations of the "Koopa Kids" more and more interesting.
So, that's when headcanons began to emerge.
HEADCANON TIME: I believe that the Koopalings, as shown in the DiC cartoons, are completely different entities from their Nintendo counterparts. They also sport distinctive personalities from their counterparts.

KOOKY (age 11), as far as his Nintendo counterpart goes, acts a lot more like Iggy than he does his own counterpart, Ludwig. While Ludwig is cool and level-headed, Kooky is pretty much insane and crazy. Ludwig doesn't take a lot of nonsense, while Kooky IS a lot of nonsense. As far as personalities are concerned, Ludwig and Kooky are complete opposites. The only thing the two really share is a certain quirk for inventing, though Ludwig isn't nearly as proficient as Kooky in this area.

KOOTIE PIE (age 16) is much more bratty than Wendy is. Wendy is also much more calm than Kootie Pie. Also, unlike Kootie Pie, Wendy can admit her own flaws. Kootie Pie's temper is much more unstable than Wendy's, but Kootie Pie's personality is also much stronger. Kootie Pie is bossier and more prideful than Wendy as well. The one thing Wendy has going for her, though, is that she's more graceful and sweeter than Kootie Pie. While Kootie Pie relies on her overwhelming personality and temper to get what she wants, Wendy goes about things in a much more underhanded way, which sometimes works out much better in the long run.

CHEATSY (age 13) is a calmer personality than rash Larry Koopa. While both rely on deception to get the job done, Cheatsy is much better at it. While Larry is mostly a small-time con artist, Cheatsy has enough finesse to make deals on the Black Market itself if he felt so led. Comparatively, Larry's like a sleazy street vendor while Cheatsy's Al Capone. Larry, though, can wrench at peoples' sympathies in a way Cheatsy can't seem to master. Since Larry's never gotten all that far, though, it's safe to say that Cheatsy's the King of Con for now.

BIG MOUTH (age 10), when compared with Morton, is much more sharp-tongued than his counterpart. Big Mouth will say what hurts. While Morton rattles off whatever comes to his head, Big Mouth is more calculative and aims for the heart with every word. Get into a fight with Morton and he's bound to forgive you within a couple of hours. Get into a fight with Big Mouth, though, and he'll be sure to make you cry.

HIP (age 6) is sweet and cute, much like Lemmy. Lemmy, though, unlike Hip, is a bit insane. Lemmy's emotional states are also a bit unstable, flying from one emotion into another if he's instigated. Hip, though, is much more innocent than his counterpart. Hip isn't angered easily and it takes a lot to get him mad (and even more to keep him that way for longer than a minute). Lemmy also isn't angered easily, but, once he's angered, he tends to stay that way for longer. Hip also is less mature than Lemmy (because, yes, that's possible) and doesn't really understand a lot about the world around him.

HOP (age 6) is pretty much nothing like his counterpart, Iggy. For one thing, Iggy is completely insane. Hop is a lot like Hip, but more timid, much unlike Iggy. Hop and Hip are as close as close can be and they can't stand being away from each other for too long. Hop also shares a curiousity of the world around him, like his twin brother. Being more timid, though, Hop tends to let Hip take the lead. While Iggy and Lemmy act pretty much independently, Hop and Hip pretty much never do.

BULLY (age 17) and Roy, on first glance, seem to share a lot of personality traits. Upon closer inspection, though, one will find that Bully is a much more calm and calculative personality than his counterpart. While Roy likes to take control, Bully likes to watch things unfold and jump in when he feels the time is best for him to do so. Roy is much hastier than Bully, not staying still for long. Roy is more overt about his actions while Bully is more underhanded. Bully likes to take things in stride and let things happen as they happen, making him a much more effective tactician.

Koopalings (left column) (c) Nintendo
Koopalings (right column) (c) Nintendo and DiC