The BEST way to do it? Use the image as a texture in a 3d program and render it out.
But only using photoshop it's a bit trickier. I've never used a filter to do it, I've always done it the old fashioned probably-more-work-than-you-have-to-do way.
You'll really only see about 1/3 of the side of the cylinder, so start with that 1/3 of the image you want "wrapped".
Take the rectangular marquee tool, put it on the left 1/3 of the portion you want wrapped, right click on the layer and choose "layer via cut"
use the free transform tool and squish it together the tiniest bit, then use the rectangular marquee tool and select a little bit less of that layer, free transform, squish... keep going until the right side will appear almost perfect but as you get close to the left it looks like its going back.
Do the same thing to the right 1/3 or so.
Marge the layers, then right click on the layer, choose blending options, then bevel and emboss. Change the color of the emboss to black so it looks like a bevel all the way around. Raise the distance/spread a bit and put the soften at max.
Right click on the sub layer for the bevel and emboss and choose "create layers."
It should create two layers above the image. Click on the one just above the layer and free transform, stretch the top and bottom so that the black doesn't touch the image at the top or bottom anymore. Hit enter, merge that layer down. Do the same for the other one.
For the text thing, start typing as normal. When the text tool still turned on, click the button to the left of the font face you are using up top. (If you are using the same version as me.) Voila. Vertical text.
If you want it so it is still in a line rather than stacked, just type normally and rotate the layer.
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