Digital alternative to underexposing and heavily pushing film?

I use photoshop. CS4 still works for me.

Do the same with digital as film.

Use manual exposure with camera.

Use RAW capture.

Process with ACR in Photoshop.

Try that.

See if it produces the results you’re after.
 
Drop the blacks/shadows so they are clipped by one or two values while increasing the whites/highlights to the verge of blowing out or even blown out. The grain is the part you will have the hardest time with. Digital noise just doesn’t do it for me after I started shooting film. I’ve not found a way to get it to look comparable to film.
 
If that's the look you're after, then you'll have to shoot film. Or, maybe close enough will be good enough for you, I don't know. But as mentioned, grain is wonderful, noise not so much.
 
Try out True Grain 2. It overlays real film grain over your image, and does a tone curve and color luminescence adjustments to replicate different black and white films. After you edit it in True Grain, you can go back into lightroom and edit it. The photo will act more like a film scan than it will a Raw file, so if you have really dark areas and try to bring them up, they'll just be grey and grainy just like a film scan.
 
Ccoppola82 said:
Drop the blacks/shadows so they are clipped by one or two values while increasing the whites/highlights to the verge of blowing out or even blown out. The grain is the part you will have the hardest time with. Digital noise just doesn’t do it for me after I started shooting film. I’ve not found a way to get it to look comparable to film.
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When converting the BW in post there are lots of processing options in Nik Silver Efex Pro. Although recently taken over by a new owner I recently read that the Nik Suite is available still for free download. One or two of the Nik Silver Efex Pro presets may give you a good place to start as some seem to emulate the look you describe though I find that more experimenting is always needed to get what I want. Some presets have the high density shadow / bright highlights / grainy look described below.

Alternatively if you prefer the look it confers a digital grain filter is one of many in the list of included filters in Nik Color Efex Pro and gives reasonable results to my eye at least though a heavily grained B/W look is not my go to "look" so you may have different ideas. I will say though that the results do not look like digital noise - it is designed to try to emulate film grain. Whether it does it well enough is a call you have to make. With Nik Color Efex you just need to experiment with the slider for amount of grain added to the image and the soft/hard grain slider (I find softer is better than harsh). If you prefer this you can just use this in lieu of the grain slider in Silver Efex by turning the grain slider off in Silver Efex and then running Color Efex after you have finished with Silver Efex.
 
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