Five Pokemon

[Adam Levine]

Smoochum
Corsola
Ho-oh
Mareep
Octillery
All from Johto.
GOLLY

 

[Limanya]

Glaceon
Omastar
Luxray
Leafeon
Yanma

Try HONKS!

 

[Sayan]

Heracross
Oshawatt
Noctowl
Kingler
Sceptile

All of them are/were Ash's Pokemon.

Now to make things difficult, try QXQYQ (it's not impossible to do).

 

[Limanya]

Quagsire
Xatu
Quilava
Yamask
Qwilfish

Try S A Y A N!
;)

 

[Porynoir]

Simisage
Aimbipom
Yamask
Aipom
Nuzleaf

KOOKY

 

[Esper]

Kingler
Onix
Omastar
Kabuto
Yanma

WATER

 

[Golurks Were Meant to Fly]

Wooper
Azumarill
Empoleon
Totodile
Remoraid

All water types mostly from the 2nd generation. (dang empoleon)

LET'S SMASH MY FACE ON THE KEYBOARD!!!!!

MCVSU Ouch. I cut my lip while doing that...

 

[Adam Levine]

Mantine
Cradily
Vaporeon
Shellder
Unown
All dwell in water except Unown.
KITTY

 

[Sayan]

Kabutops
Ivysaur
Tentacruel
Toxicroak
Yanmega

All are Stage 1 Pokemon (evolved once).

Now try YOYOY.

 

[Limanya]

Yanma
Omanyte
Yamask
Onix
Yanmega

Try Rose L. (Rose Lalonde!)

 

[Sayan]

Rhyperior
Onix
Swampert
Excadrill
Larvitar

5 dual typed Ground types, each from a different generation.

Next word is PIZZA.

 

[Golurks Were Meant to Fly]

Pachirisu
Illumise
Zapdos
Zebstrika
Ampharos

Almost all electric types from all different generations. I guess illumise kinda counts cuz uh... fireflies are electric?

IDIOT

 

[Limanya]

Illumise
Delibird
Igglybuff
Oddish
Timburr

All are Pokemon that have something to do with the Exiles from Homestuck.

Try Dave S. (Dave Strider, yeah!)

 

[Avishka]

Delibird
Ampharos
Vaporeon
Emolga
Swampert

G O O F Y

 

[Sayan]

Grumpig
Omastar
Octillery
Ferrothorn
Yanmega

All of them have evolved once and can't evolve further. Each is from a different generation.

Now try JOHTO

 

[Limanya]

Jumpluff
Octillery
Heracross
Togetic
Omastar

Almost all of them are from Johto!

Jade H. (Jade Harley)

 

[Sayan]

Jirachi
Azelf
Duosion
Espeon
Hypno

Psychic types, each from a different generation.

Next set of letters is UNOVA.

 

[Golurks Were Meant to Fly]

Unfezant
Ninjask
Oshawott
Venipede
Alomomola

All gen 5 except for ninjask because APPARENTLY unova is too cool for pokemon whose name starts with N... wait. Can I count N as a pokemon?
O.o

WHOAA

 

[Limanya]

Wailmer
Houndour
Omanyte
Aipom
Anorith

All are the first stage of a two-staged evolution line.

John E. (John Egbert)

 

[classiccartoonsftw]

Jynx
Omastar
Hypno
Ninetales
Exeggutor

They're all fully evolved Pokemon from two-staged evolution lines.

How about: MARIO