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Of every generation, the first is always the best.
Prefix will help your station, given free without jest.

The infix is a hoot, you'll be thrown for a loop.
It's what you did with fruit, you'll see the cars swoop.

My suffix can help you paint, or sail the open seas.
Under where mens' eyes aint, protects girls when they sneeze.

So you think you know what I am, tell me, I've worked with Sam.

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  • 1
    $\begingroup$ This is an interesting puzzle, because I think I've just taken the bait... $\endgroup$ – El-Guest Aug 31 '18 at 14:41
  • $\begingroup$ Well, I was hoping someone would :P $\endgroup$ – Joe-You-Know Aug 31 '18 at 14:42
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    $\begingroup$ Hook, line, sinker. $\endgroup$ – Perpetual J Aug 31 '18 at 14:47
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Are you a

FREIGHTLINER?

Of every generation, the first is always the best.

This refers to the first generation of Transformers, in which Optimus Prime transformed into a Freightliner semi truck.

Prefix will help your station, given free without jest.

FREIGHT is the prefix, which will help your station by keeping it busy? Also, it could be FREI, the German word for FREE.

The infix is a hoot, you'll be thrown for a loop.

A literal loop, since the infix is a figure EIGHT.

It's what you did with fruit, you'll see the cars swoop.

Similar to fruit, in French, EIGHT is huit. The cars swoop around figure 8 tracks? (Dangerous!)

My suffix can help you paint, or sail the open seas.

A LINER can help people paint (ie. next to windows, or mouldings); an ocean LINER sails the open seas.

Under where mens' eyes aint, protects girls when they sneeze.

Men tend not to wear eyeLINER; and it protects girls from drippy makeup when they sneeze? Update from @Joe-You-Know: This was apparently referring to "a Panty Liner. Women, especially after having their first child, you know what, I think I don't need to explain it any further than that..." Thanks, @Joe-You-Know!! :D

So you think you know what I am, tell me, I've worked with Sam.

Optimus Prime worked with Sam Witwicky in the Transformers movie.

The secret hint is

OPTIMUS, the acrostic which refers to OPTIMUS PRIME, the leader of the AUTOBOTs.

The title refers to

AUTOBOTS VS DECEPTICONS, the ultimate Transformers battle, including between the leaders Optimus Prime and Megatron.

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  • $\begingroup$ I'd love to see the explanation for this because it is correct. $\endgroup$ – Joe-You-Know Aug 31 '18 at 14:48
  • $\begingroup$ @Joe-You-Know Explanation is here now! Always plenty of lines for me to add detail to :D Great puzzle!! $\endgroup$ – El-Guest Aug 31 '18 at 14:50
  • $\begingroup$ I'll explain my reasoning on some of these. Under where mens' eyes aint, protects girls when they sneeze, is referring to rot13(n Cnagl Yvare. Jbzra, rfcrpvnyyl nsgre univat gurve svefg puvyq, lbh xabj jung, V guvax V qba'g arrq gb rkcynva vg nal shegure guna gung...) $\endgroup$ – Joe-You-Know Aug 31 '18 at 14:52
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Are you an

AUTOBOT? Everything except the affix riddle seems to point to this....which means it's likely wrong...

Of every generation, the first is always the best.

The first generation of Autobots is the best.

Prefix will help your station, given free without jest.

AUTOs are needed to populate a station (gas station, etc). Also automation will help to improve the efficiency of a station.

The infix is a hoot, you'll be thrown for a loop.

O might be the infix, since it's a literal loop?

It's what you did with fruit, you'll see the cars swoop.

This could be Fruit O' the Loom? Or these, Meijer Frosted Fruit-Os

My suffix can help you paint, or sail the open seas.

BOTs are really good at doing both of these things.

Under where mens' eyes aint, protects girls when they sneeze.

Haha, you said "underwhere" -> "underwear" -> BOTtoms?

So you think you know what I am, tell me, I've worked with Sam.

Sam Witwicky was the main human character who worked with the AUTOBOTs in transformers.

The secret hint is

OPTIMUS, the acrostic which refers to OPTIMUS PRIME, the leader of the AUTOBOTs.

The title refers to

AUTOBOTS VS DECEPTICONS, the ultimate Transformers battle, including between the leaders Optimus Prime and Megatron.

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  • $\begingroup$ Excellent guess, but as you surmise, this is not the answer I'm looking for. Though this is definitely in the right direction. $\endgroup$ – Joe-You-Know Aug 31 '18 at 14:44
  • $\begingroup$ Also, rot13(fjbbc pbhyq or ersreevat gb gur dhvpx genafvgvba sebz iruvphyne sbez). Great answer! $\endgroup$ – Perpetual J Aug 31 '18 at 14:46

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