I feel bad for you; you're going to get so many suggestions!

Fortunately, they are all likely good suggestions; it'll just be overhwelming.

I'll throw my advice in; it'll likely mirror what others are saying.

I like shopping at smokingpipes.com

They have a good selection of tobacco, and for most pipes, they photograph the actual pipe you will receive.

Pipe - I recommend you get him a corn cob pipe.

Missouri Meerschaum is the brand. You can order directly at corncobpipe.com or look on smokingpipes.com

A corn cob is the ideal pipe to learn on. They are innexpensive at roughly $20-$30, and he will always have a use for it when testing new tobacco.

If your budget allows to get him two pipes, then I would look at the brands below for a nice briar(wood) pipe.

Savinelli - They make great high-quality pipes. New, they're around $120 for a base model. (They have different levels or grades of pipes that get very expensive. Ignore those.)

Rossi - For a good mid tier briar pipe, their sister company, rossi, is just as well made but may have less aesthetically perfect wood. They sell for around half as much but smoke just as well.

There are other brands like Ropp and Peterson, but I have less experience with them.

Tobacco - There are many different types of tobacco. And within those types, there is a variety. It gets complicated quickly. I suggest you get him at least one of these three types so he can see what he likes.

Virginia blend - Briar Fox $11

English blend - Peterson Nightcap $15

Aromatic - Lane Limited 1-q 2oz $5, Red Blood Moon $11

There are definitely a lot of tobacco types not represented here, but this is a wide enough variety that it will expose him to what's out there.

Accessories - He will need a few accessories like pipe cleaners, tamper tool, and lighter. It's also nice to have a pipe rest/stand and ashtray, but it is not necessary.

Pipe cleaners - Smokingpipes has a good selection $2-$3

Tamper tool - Czech pipe tool $2

Lighter - He probably has one, but anything with a soft flame, i.e not a butane torch lighter.

That's the basics! Those tobacco recommendations are pretty general based on what I saw in stock at smokingpipes. The main point is to try to get one of those three types for him to try.

If you go to a local tobacco store, they will usually set you up with tobacco samples, which is probably the ideal option.

Good luck!