Five Pokemon

[The Doctor]

Roggenrola
Omantye
Tirtouga
Flareon
Lileep

All Rock Pokemon except Flareon becuase there are no Rock Pokes beginning with F

CLOTH

 

[Adam Levine]

Combee
Lopunny
Octillery
Tangrowth
Honchkrow
All of these are my favorite Pokemon, except Octillery, too bad no Sinnoh Pokemon start with "O". :(
How about:
STUFF

 

[Golurks Were Meant to Fly]

Staraptor
Togetic
Unfezant
Fearow
Farfeth'd

All normal/flying types, almost from all different generations.

SOKKA

 

[Squirrel]

Shelder
Onix
Kakuna
Krabby
Armaldo

All of the above are capable of learning moves to increase their defenses. c:

RAGES

 

[Avishka]

Rotom
Armaldo
Gallade
Espeon
Shelder

SMILE

 

[TRiGa]

Smoochum
Muk
Igglybuff
Ledian
Eelektross

EEVEE

 

[Avishka]

Eevee
Espeon
Vaporeon
Emolga
Entei

MUSIC

 

[blackmorale]

Milotic
Ursaring
Sceptile
Illumise
Claydol

Try PICHU.

 

[Golurks Were Meant to Fly]

Pansage
Ivysaur
Camurupt
Hippopotas
Ursaring

All resist or are imune to Pichu's electric attacks...plus a random bear.

GLOOM

 

[Squirrel]

^ The bear thing made me lol.

Goldeen
Lumineon
Omanyte
Octillery
Mudkip

They're all slippery wet Water types! <3

Next 5 letters: BLAZE

 

[Golurks Were Meant to Fly]

Blitzle
Luxio
Ampharos
Zapdos
Electrike

Electric types all from different generations.


BROCK

 

[TRiGa]

Boldore
Roggenrola
Onix
Cranidos
Kabutops

Misty

 

[xSkullKing16x]

M: Mantyke
I: Ivysaur
S: Servine
T: Torkal
Y: Yanma

New word: Delta

 

[Golurks Were Meant to Fly]

Ditto...... : )

Emolga...... : D

Lickitung......... : P

Throh............ ) : (

Azurill...... : (

They all have emoticon faces.

EMOTE

 

[xSkullKing16x]

Emboar
Moltres
Octillery
Typhlosion
Excadrill

Color

 

[classiccartoonsftw]

Cubone
Omanyte
Lickitung
Onix
Rattata

All of them are first stage Pokemon with just one evolution.

Try this one: BRONY

 

[xSkullKing16x]

Brellom
Roserade
Octillery
Ninjask
Yanma

How about "NOOBS"

 

[Limanya]

Natu
Omantye
Octillery
Bidoof
Stunfisk

Derpy 'mons.

GLARE

 

[footontable]

Natu
Omantye
Octillery
Bidoof
Stunfisk

Derpy 'mons.

GLARE

G | Galade
L | Lunatone
A | Arceus
R | Roselia
E | Electross


Try this Ducky :bandit:

 

[Golurks Were Meant to Fly]

Dodrio
Ursaring
Cinccino
Kanghaskan
Yamask

Almost all 1 evolution family normal pokes except for kanghaskan and a random ghost (this time not a bear!)

SCHMO(yoho)