Chevy 350

[CAP1]

I'll second the suggestion of Fel-Pro gaskets. I'll go a step further, and suggest better than cheap replacement head bolts, and replacing both head gaskets if you intend to keep the truck. I'd not only check the heads for cracks, I'd have them surfaced, and at least have the valve stem seals replaced. I also suggest Permatex hi temp O2 safe RTV silicone. You cannot get parts too clean, gasket surfaces need to be clean and perfect. Torque the heads to 25, 50, and then 75, with oil under the heads of the bolts, Teflon sealer on the threads, and use a real torque wrench, not one of those cheap "wonder wands" they rent at the cheap parts house.

 heheheh.....i still have one of those "wonder wrenches" out in my garage, from about 30 years ago. at the shop, i just bought a new clicker. couldn't afford the digital one i wanted.......

[Masherbrum]

also......need the 8th digit of the VIN. if it's a 99 silverado, you don't have a 350, unless it came outta something else...according to my info system, you've got a 4.3 v6, 4.8 v8, or a 5.3 v8

 looking at the procedure right now. you don't have the option with the head bolts......it specifies to replace them.....
Cylinder Head Bolts (First Pass all M11 Bolts in Sequence)
   

30 [n-m]
   

22 lb ft

Cylinder Head Bolts (Second Pass all M11 Bolts in Sequence)
   

90 degrees

Cylinder Head Bolts (Final Pass all M11 Bolts in Sequence-Excluding the Medium Length Bolts at the Front and Rear of Each Cylinder Head)
   

90 degrees

Cylinder Head Bolts (Final Pass M11 Medium Length Bolts at the Front and Rear of Each Cylinder Head in Sequence)
   

50 degrees

Cylinder Head Bolts (M8 Inner Bolts in Sequence)
   

30 [n-m]
   

22 lb ft

They made the C/K's in 99 and it would have the VIN R motor.

[CAP1]

yep. got it. 

[Captain Virgil Hilts]

 heheheh.....i still have one of those "wonder wrenches" out in my garage, from about 30 years ago. at the shop, i just bought a new clicker. couldn't afford the digital one i wanted.......

I have a couple of Snap On dial types (2% certified) and a click type Snap On (with the knob on the side, not a twist handle, 2% certified) that I've had for years. Neither has ever tested outside the tolerances. I'm not big on the digital torque wrenches, but I suppose they're okay, the ones with an alarm can be used on flat rate work like a click type.

[CAP1]

I have a couple of Snap On dial types (2% certified) and a click type Snap On (with the knob on the side, not a twist handle, 2% certified) that I've had for years. Neither has ever tested outside the tolerances. I'm not big on the digital torque wrenches, but I suppose they're okay, the ones with an alarm can be used on flat rate work like a click type.

 a guy i used to work for had a snap on digital. it always seemed accurate. i don't know what tolerances he'd had it tested to though. i hated digging into his tools though, so i generally used my matco clicker. the first time i'd used his, i forget what i was working on, but mine clicked as if i'd reached the torque it was set to.....but it didn't "feel" right. as if i wasn't pulling with enough force. so i got his out, and sure enough, mine was going off too soon.
 i sent it out, to get repaired. that was 10 years ago. it just started that crap again about 6 months ago, so i just bought a new one this time.