Two that you can't possibly go wrong with ... and I will bet my life on it!

The Artuto Fuente Double Chateau Sun Grown (if you enjoy longer smokes) or the Chateau Fuente Sun Grown (if you prefer shorter cigars) ...

Heck ... spend another $14 over $100 ... and go with the Cuban Belicoso SG !!!

That will definately leave a mark ...

Words of Wisdom Slim!!

Irish,
If these are for a Bachelor's bash, buy two $50 boxes. One fuller and one mild.
I don't know the crowd, but many guys who don't usually smoke will appreciate the milder cigars, while real smokers will likely bring their favorites anyhow.
Also, look for brands that guys will know. The casual smoker tends to like name recognition. So they will enjoy an R & J more than a Mayorga simply because they've heard of them before.
I often organize bus trips for football roadtrips and find that this process works out quite well.
And be sure to bring at least one dog rocket for the stripper to ruin...

One line of cigars that you don't hear much talk about ... are the Flor de Ybor City cigars.

These are bundled cigars ... and can be had for a steal! Prices range from $25 to $58 a bundle, and come in 11 different sizes.

Flor de Ybor City cigars are made from the best tobaccos manufactured with skilled painstaking workmanship by master craftsmen with a lifetime of experience in the blending of the finest tobacco to give a mild, rich, satisfying, full flavored taste for those who care to achieve a new plateau in cigar smoking pleasure.

Once you light up a Flor de Ybor City cigar, you'll discover that it will satisfy your expectations every time. All cigars are bundled in packs of 20 and come with either a Connecticut Shade natural wrapper or Connecticut Broadleaf Maduro wrapper, except for the No. 85, which is rolled with an Ecuadorian Sun Grown natural wrapper.

These cigars are all manufactured by Tabacalera A. Fuente y Compania.

Jazz

Yes, I have been lucky enough to have two of the Ipanemas and they are about as good as it gets. The first one I had lasted at least 1 hr and 30 to 45 minutes and was one of the very best cigars I have ever had.

Wifey has my credit cards under close scrutiny so I cannot buy anything that expensive for a while, wish I could I would have a box or two of Brazilas resting in humidor. CAO's are the very best in my view, and I feel the Brazilas are my favorites in the entire line of greatness.

Charlie

Quite a few good suggestions already ... one thing to keep in mind as you finalize the plan, is that there's a wide spectrum of taste to allow for in any group, but that's particularly true if there's to be a lot of guys who aren't regular cigar smokers ... if budget permits, you might want to consider having a mild, a medium and a full-bodied choice available ... some I'd recommend in the mild are CAO Gold, Toraño Reserva Selecta or Nicaragua Selection or for a little touch of faux prestige (and who's to know it's faux?), get some of those Maxim's de Paris ... they're decent cigars, and mild enough for a baby to smoke ... plus, when you tell those non-smokers this is a cigar that was especially designed for the famous "maxeem's" restaurant in Paris where they were sold at absolutely outrageous prices, ... well, you get the point.

For guys who have done some cigar smoking, mix and match from stuff such as ... Onyx Reserve maddies, Perdomo Estates, Toraño Exodus 59s or Sigs, CAO Brazilias, ERdMs, La Aurora, LGCs, Oliva "O", Padron, Sancho Panza, and R&J ...

go to the CI site and do a little snooping around .. betcha there's a double digit long list of other good choices I've not thought of right off the top of my head ... there's just SO many decent smokes for less than $100 a box ...

I like most of the ideas here. My cheap a$$ self would toss some $15 bundle type cigars at the guys who never smoke, but will in a group. Those who want to sample something and might get into cigars....up the ante a bit. And if you have some refined tastes in your group...then you offer up the good stuff. All in all a good variety will run you less than $100 and you'll have some change left over for a bottle of Jack.

Without a doubt, the Padron 2000 or 3000 (depends on your size preference) Maduro. Super cigar that does not disappoint.

Jim