Five Pokemon

[Cardinal]

Drifblim
Infernape
Tyranitar
Torterra
Octillery

BONSLY

 

[AlexMonroe]

Thats . . . almost five letters. I suppose. Good . . . try?

I'll go with the "BONSL" part.

Butterfree
Octillery
Nidoran M
Slugma
Lapras

I'll go with . . . MEATY

 

[mineox100]

Monferno
Empoleon
Abomasnow
Terrakion
Yanmega

Next up is:
YAHOO

 

[Avishka]

Yanmega
Ariados
Haunter
Oshawott
Oddish

FORUM

 

[Golurks Were Meant to Fly]

Foongus
Oddish
Roselia
Ursaring
Meganium

Almost all grass/poison types from different generations except for Meganium and a random bear. :/

SILLY

 

[AlexMonroe]

Starmie
Illumise
Larvitar
Lileep
Yanmega

Each one is super effective against the last in some way

Next is WHOSE

 

[TheFattestSnorlax]

Whimiscott
Houndour
Oshawott
Snorlax
Entei

Hmmm...how about SMART.

 

[mineox100]

Serperior
Monferno
Ariados
Raichu
Tauros

Next is... PKMON

 

[Seventh Sea]

P- Phanpy
K- Krokorok
M- Mamoswine
O- Onyx
N- Nidoking

All ground types!
so...

EARTH

 

[Avishka]

Entei
Ariados
Raichu
Tauros
Houndour

Next is OCEAN

 

[blue]

Omastar
Cradily
Exeggcute
Amoonguss
Nuzleaf

All grass type Pokémon!

Let's try: Chair

 

[Golurks Were Meant to Fly]

Cacturne
Hop-Hip
Amoongus
Ivysaur
Roserade

Dual grass types from all different generations,

GRASS

 

[mineox100]

Gardevoir
Raticate
Arcanine
Sawk
Serperior

All mono-types!

Try... BERRY

 

[ShadowTsuki]

Banette
Electrike
Rotom
Raikou
Yamask

Lets Try SPARK

 

[Golurks Were Meant to Fly]

Beautifly
Escavalier
Reshiram
Rufflet
Yanmega

All 5th gen dual types except for yanmega. There ARE only three pokemon names starting with Y :/

ZORUA

 

[Scultr]

Zoroark
Oddish
Roggenrolla
Uxie
Alakazam

SNARL

 

[Golurks Were Meant to Fly]

@Klinklang5 uh... I'm not sure you read the rules too thoroughly... :D

But I will do one from ShadowTsuki that got ninja'd (by me)

All electric types to go with the electric themed word.

Shinx
Pika...nope! Plusle.
Ampharos
Rotom
Kecleon (it becomes electric with color change?)

SHINX

 

[The Doctor]

Sawk
Happiny
Igglybuff
Ninjask
Xatu

GAMES

 

[classiccartoonsftw]

Gallade
Alakazam
Metagross
Espeon
Sigilyph

Psychic Pokemon from every generation!

EDIT: How about: ABOUT

 

[Golurks Were Meant to Fly]

...that's insulting and derogatory and just overall not funny in the slightest.
I'll do the last five letter word you typed before the alleged word.

Archen
Bastiodon
Omanyte
Ursaring
Tirtouga

All fossil pokes, plus a random bear.

ROTFL