Help with Tiny Bullet

[cyberborikua]

Found these two bullets the bigger one seems modern, but do not know the caliber. The tiny one may be old. Is that possibly the size of the smaller bullet (1/4") or does it have a missing piece? Any ideas about the era it might belong to?

 

[d2]

Looks like a .45 on the left and a .22 on the right...d2

 

[cyberborikua]

Looks like a .45 on the left and a .22 on the right...d2

Thanks. What era do you think is the .22 one?