The strangest nickname thing for me was when, back in the days of Red and Blue, I let my brother catch whatever he wanted in the Safari Zone. When I went back to play my game after he was done, I had boxes filled with different Safari Zone Pokémon named "DUDE". Still not sure why he did that.
Anyway, as far as things I've named my Pokémon:
Smartlass - A nickname given to a Frosslass that I won all the Smart Contests with. Probably the one I'd consider my closest attempt at being "clever".
Arcawarior- In every main game for a Generation (the one I play most for that generation, in other words), I give this nickname to an Arcanine. Back in Blue (or Red?) I experienced a glitch where a Haunter I had nicknamed "BLACK FOG" evolved into a Growlithe at Lv.50. Upon evolving, it knew Flamethrower, Surf, Surf again, and something else. Since my Blue (or Red?) reset itself, I name an Arcanine after it in each Generation, to keep its memory alive.
Mrs. Mime - Of course, a nickname given to a female Mr. Mime. (And yeah, I know its Japanese name isn't Mr. Mime.)
Tentacool2 - A nickname given to the second shiny Tentacool I found in Sapphire.
Itemfinder - A Yanma I had in Platinum. It was used in the first slot of my party and I always knocked it out. Used together with "Friskerton" below.
Friskerton - The nickname for my Frisk Banette, which would be in the second slot of my party after "Itemfinder", the Yanma. These two were best buds and I used them together during my giant quest to get as many wild hold items as I wanted. The name is supposed to sound sophisticated, as he is a fancy old man who steals things... I guess. Imagine a Banette with a monocle, top hat, and white curly moustache.
BLUEAURA - The nickname given to a Dragonite from the Generation 3 days. I used it in the Battle Tower and defeated the Tower Tycoon with it.
ORANGEAURA - The nickname given to a Salamence in Platinum. I wanted a "rival" to BLUEAURA. It and BLUEAURA now sit together in my SoulSilver game, and will most likely be carried through all the following Generations together.
Magma Duck - The nickname given to one (male) Magmar each Generation. There was a time back in the Generation 1 days where I traded all these kids at a baseball field Magmar, because they didn't have it yet. There was this line of tiles in Cinnabar Mansion that I thought yielded more Magmar (and they seemed to), so I ran up and down there catching a bunch. I named one of the ones I caught Magma Duck, so that's where that comes from.
Lunos, Luna, Lunos Jr. - Nicknames given to a "family" of Absol in my Generation 3 days. Lunos was the dad, Luna was the mom, and Lunos Jr. was one I bred from them. Lunos was awesome, and is the main reason I like Absol. Each of them had interesting moves (sadly Generation 3 wasn't the best time for Absol's movepool), like Lunos's Flamethrower, or Luna's Aerial Ace. There was also a Lunatone I nicknamed "Luna Guard". It was kinda like the family guardian.
Zang - A nickname given to a Zangoose in each Generation. I had an awesome Zangoose in Generation 3 (much like my "awesome" Absol, I just loved them a lot and they weren't good competitively) nicknamed Zang.
Vipe - The enemy of Zang, a Seviper named Vipe. So original, I know. xD
Sir Pin - A nickname given to a Pinsir in Platinum. I went back and played Blue a while after naming this Pinsir, and I was amazed to find out I had named a Pinsir "Sir Pin" in one of my boxes. Even way back then I thought it was a cool nickname for a Pinsir. xD It must've been stored in the back of my brain, or something.
ULTRADRILL - A nickname given to a Nidoking that was on my in-game team in Blue. One of my all-time favorite Pokémon even to this day. I remember it had Rock Slide and Ice Beam, but I forget the other moves. My friend and I made evolutions for Nidoking and Nidoqueen in the Generation 1 days, and my ultimate Nidoking evolution was named Ultradrill, so that's where that comes from.
Galledge - A nickname given to a Gallade I wanted to train in Platinum. Just thought it sounded cool.
Magna Fire - The nickname given to my Typhlosion in Silver (and one I had in Generation 3). It wasn't until recently that I realized its name is basically "Magnifier". >_>; Definitely not what I had intended.
Minus, Plus - Nicknames I give to one Minun and one Plusle each Generation.
Kekks - A nickname I give to one Kecleon each Generation.
Spotz - A nickname I give to one Spinda each Generation.
Mod Synch - A nickname I give to a Modest Synchronize Abra in each game. I always try to find one. xD
... And there are many more, unfortunately. >_>; I guess a lot of my nicknaming habits come from Generation 3, where I spent a lot of time catching a nicknaming odd Pokémon.
Anyway, as far as things I've named my Pokémon:
Smartlass - A nickname given to a Frosslass that I won all the Smart Contests with. Probably the one I'd consider my closest attempt at being "clever".
Arcawarior- In every main game for a Generation (the one I play most for that generation, in other words), I give this nickname to an Arcanine. Back in Blue (or Red?) I experienced a glitch where a Haunter I had nicknamed "BLACK FOG" evolved into a Growlithe at Lv.50. Upon evolving, it knew Flamethrower, Surf, Surf again, and something else. Since my Blue (or Red?) reset itself, I name an Arcanine after it in each Generation, to keep its memory alive.
Mrs. Mime - Of course, a nickname given to a female Mr. Mime. (And yeah, I know its Japanese name isn't Mr. Mime.)
Tentacool2 - A nickname given to the second shiny Tentacool I found in Sapphire.
Itemfinder - A Yanma I had in Platinum. It was used in the first slot of my party and I always knocked it out. Used together with "Friskerton" below.
Friskerton - The nickname for my Frisk Banette, which would be in the second slot of my party after "Itemfinder", the Yanma. These two were best buds and I used them together during my giant quest to get as many wild hold items as I wanted. The name is supposed to sound sophisticated, as he is a fancy old man who steals things... I guess. Imagine a Banette with a monocle, top hat, and white curly moustache.
BLUEAURA - The nickname given to a Dragonite from the Generation 3 days. I used it in the Battle Tower and defeated the Tower Tycoon with it.
ORANGEAURA - The nickname given to a Salamence in Platinum. I wanted a "rival" to BLUEAURA. It and BLUEAURA now sit together in my SoulSilver game, and will most likely be carried through all the following Generations together.
Magma Duck - The nickname given to one (male) Magmar each Generation. There was a time back in the Generation 1 days where I traded all these kids at a baseball field Magmar, because they didn't have it yet. There was this line of tiles in Cinnabar Mansion that I thought yielded more Magmar (and they seemed to), so I ran up and down there catching a bunch. I named one of the ones I caught Magma Duck, so that's where that comes from.
Lunos, Luna, Lunos Jr. - Nicknames given to a "family" of Absol in my Generation 3 days. Lunos was the dad, Luna was the mom, and Lunos Jr. was one I bred from them. Lunos was awesome, and is the main reason I like Absol. Each of them had interesting moves (sadly Generation 3 wasn't the best time for Absol's movepool), like Lunos's Flamethrower, or Luna's Aerial Ace. There was also a Lunatone I nicknamed "Luna Guard". It was kinda like the family guardian.
Zang - A nickname given to a Zangoose in each Generation. I had an awesome Zangoose in Generation 3 (much like my "awesome" Absol, I just loved them a lot and they weren't good competitively) nicknamed Zang.
Vipe - The enemy of Zang, a Seviper named Vipe. So original, I know. xD
Sir Pin - A nickname given to a Pinsir in Platinum. I went back and played Blue a while after naming this Pinsir, and I was amazed to find out I had named a Pinsir "Sir Pin" in one of my boxes. Even way back then I thought it was a cool nickname for a Pinsir. xD It must've been stored in the back of my brain, or something.
ULTRADRILL - A nickname given to a Nidoking that was on my in-game team in Blue. One of my all-time favorite Pokémon even to this day. I remember it had Rock Slide and Ice Beam, but I forget the other moves. My friend and I made evolutions for Nidoking and Nidoqueen in the Generation 1 days, and my ultimate Nidoking evolution was named Ultradrill, so that's where that comes from.
Galledge - A nickname given to a Gallade I wanted to train in Platinum. Just thought it sounded cool.
Magna Fire - The nickname given to my Typhlosion in Silver (and one I had in Generation 3). It wasn't until recently that I realized its name is basically "Magnifier". >_>; Definitely not what I had intended.
Minus, Plus - Nicknames I give to one Minun and one Plusle each Generation.
Kekks - A nickname I give to one Kecleon each Generation.
Spotz - A nickname I give to one Spinda each Generation.
Mod Synch - A nickname I give to a Modest Synchronize Abra in each game. I always try to find one. xD
... And there are many more, unfortunately. >_>; I guess a lot of my nicknaming habits come from Generation 3, where I spent a lot of time catching a nicknaming odd Pokémon.