Two choices

[MCS]

Diamond

Emoticon | Smiley

 

[Gumball Machine]

emoticon

FireRed/LeafGreen

 

[MCS]

LeafGreen

Koffing | Weezing

 

[Gumball Machine]

Neither, don't use poison-types.

HeartGold/SoulSilver

 

[MCS]

HeartGold

Charmander | Charizard

 

[Gumball Machine]

Charizard since it can fly.

Partners In Time/Bowser's Inside Story

 

[New Super Mario]

BIS

Lubba/Luma

 

[yoshidude99]

funny farting

Chugaconoroy/Nintendo Caprisun

 

[ralphfan]

Chuggaaconroy

Oprah | Tyra Banks

 

[New Super Mario]

Oprah

Dr. Phil/Ellen

 

[MCS]

Ellen

Bill Nye | Ellen

(they're both at this Disney ride)

 

[Gumball Machine]

Bill Nye (the science guy)

Ludwig/Larry

 

[Xiahou Ba]

Ludwig

Nintendo|Sega