The blue Side Burn from the 1st wave of RID. I saw it in a comic shop not realising at the time Transformers were still going and had to buy it for the nostalgia value. Upon opening it, my first reaction was simply "wow I don't remember TFs being so poseable". I went on to buy everything I could find from RID, then Armada and the re-issues came along and the obsession started.

My first toy as a collector was RID Prime, as a kid it was Sandstorm i think.

BW2 God neptune, I never even got the gestalt parts but he just seemed so cool that got a couple of G1 gestalt KOs off ebay.

 

Some time passed after that, one day I saw Tidal Wave and then everything changed.

 

As a kid I think G1 Ultra Magnus was the first, I also had slingshot and doubledealer, but I lost them all.

around 1998 i discovered E-bay... and Hot Rod.. been collecting ever since

G1 Divebomb mib off ebay.

As a kid - Trailbreaker in 1984.

1988 - all TFs vanish. Red alert used as a (!!!) Doorstop. to paint a door.

As a collector - BW OpOp in 1998.

currently missing 5 from the old collection

deluxe jetsorm at walmart (was looking for billiard chalk)

As a kid, Warpath ans Optimus Prime. (Warpath before dinner, Prime as an after dinner surprise.)

 

As an adult, TRU Ultra Magnus Reissue. (After finding a near mint G1 Shrapnel on a job cleaning out an old paint store, a few years prior. Asked the store owner, they said some kid left it there years ago, and I could have it. FREE! :thumb)

I don't distinguish between "collecting" and "buying because I like them and want to play with them." So for me it would be Soundwave & Buzzsaw in 1985.

Bumblebee, for the minis.

 

Mirage and trailbreaker, for the autobot cars.

 

Optimus Prime, for the leaders.