I revised this from the original to include food choices and update some of my picks, which have changed over time. I'll also post some explanatory notes where needed. Here we go:
Ok guys, here's something with a lot more choices and a lot less restrictive. Please play by the rules, huh? The rules have been designed to make it both fun and challenging at the same time. I don't want to see any "I couldn't restrict myself to just 5 items" garbage.
Work at it! 
Come on, this is fun because we're picking things that have nothing to do with D&D as well as D&D stuff, so we should see some interesting picks from people here.
Here's the premise. The world goes to hell in a hand-basket like in the Night of the Living Dead trilogy. You get to escape to an isolated, deserted island somewhere, or some other hidden, inaccessible place.
You are going to spend the rest of your life there, and you can assume you have your immediate family and/or a handful of friends there with you. In any case, a reasonably sized group of people probably not to exceed 12 members.
You get to pick five items from each category below. I will list the specifics for each one under their respective categories, but they're all going to give you a wide variety to choose from. The only difficult part may be narrowing it down to just 5 choices. But that's what makes it challenging.
Here we go...
Advanced Dungeons & Dragons Games
You get to pick five published paper products from OD&D, BD&D, AD&D, or other games by TSR (Gamma World, Star Frontiers, etc). You cannot pick the AD&D Core Rules 2.0 on CD or anything like that. Each item must be a paper, published item. It can also include Judge's Guild material. I changed this category from the original because to play AD&D you really must pick the PHB, DMG, and MM or MCs, as a base. That takes up 3 of the 5 choices automatically. So I changed this to 5 of any other AD&D items. You can pick modules, box sets, anything. But they must be 5 distinct items. Assume you have access to pencils, character sheets, and dice, along with the DMG, PHB, and MM or MMI & MMII.
Board Games
Let's face it, sometimes we need a break from D&D. So, any 5 board games or other non-video games will be allowed. Video games will have their own choices in the arcade section. To qualify for this, it must be a game of some sort, preferably with a board. Checkers, Monopoly, Chess, Don't Break the Ice, Candyland, Ouija boards, etc. are all workable type choices. A game is different than a toy in that a game has rules, a toy does not.
Video Games
Any 5 video or computer game that exists. It'd be nice to indicate whether the one you pick is an arcade game (free standing like in an arcade or Atari/Intellivision style home version, doesn't matter) or a computer video game. Assume you have something to play it on.
Music
You get to pick any 5 albums. You cannot pick a "Best of..." album or a "Greatest hits" album. Double sets like Pink Floyd's The Wall count as one pick even though they have 2 CDs to cover it all. However, double sets or anthologies like the Beatle's Blue Album 1967-1970 or Beatles Anthology cannot be chosen. Soundtracks for movies count as 1 pick. Come to think of it, let us know if you want it on CD, vinyl, tape, or 8-track. Assume any format will last forever.
Books
Any 5 books ever published, except D&D game material from any version or edition. Again, compilations don't count. So you could not pick a book like "Stephen King's 10 Best Stories Ever", but you could pick a book like the ones that collect the various short stories by HP Lovecraft. I think it's pretty clear what we're shooting for with these rules by now.
Toys
Any individually sold toy counts. No "I want the entire Star Wars collection" ideas. Toys are any play thing not considered a game. Stuff like hula hoop or superball can count as a toy instead of a game. Games have rules, toys do not.
DVD Movies
Same thing here. A double set like Count Yorga/Return of Count Yorga which has 2 movies on one disc counts as two movies. Those 10 packs of horror movies or 20 kung fu movies in a box cannot be counted unless they contain no more than 5 movies, and that counts as your 5 picks. No compilations or stuff like that. The Star Wars trilogy counts as 3 movies. Each individual movie counts as one pick. Assume that any movie you want to have on DVD is out on DVD whether it's ever actually been released on DVD or not. If you choose a tv show on DVD, and that tv show comes in seasons, each season counts as 1 pick.
Comic Books
Any defined story line counts as one pick. For example, you could pick an ongoing, continuous story line that ran across 6 issues of Spiderman, but you could not pick Spiderman #1 - 50. No fair picking "The entire original run of the Justice League of America". If a comic title lasted less than 25 issues, you can choose it as one pick. No "best of" stories or collections. Stuff like the Frank Miller Daredevil graphic novel reprints count as one each unless they contain more than 25 reprints where each was its own individual issue. This one gives you a lot of leeway.
Foods
Any individual recipe can count as one choice, for example beef fried rice or chicken cacciatore. Likewise, any individual food can count as one choice, for example, bananas or BBQ potato chips. Assume no matter what you choose -whether actually healthy food or actually junk food, your choices will keep you healthy and provide all nutrients needed.
Make sure you use each category listed here in order.
Choose wisely, because this stuff is going to have to last you a lifetime!
Ok, here's my picks.
Dungeons and Dragons Games
1. Deities & Demigods (1E)
2. City of Skulls (Greyhawk, 2E)
3. FR10 Old Empires (FR, 1E)
4. Forgotten Realms Campaign Setting (1E Gray Box)
5. Ruins of Undermountain
Board Games
1. Monopoly
2. Green Ghost
3. Ka-Bala
4. Life
5. Aggravation
Video Games
1. Space Invaders (free standing arcade game)
2. Tempest (free standing arcade game)
3. Asteroids (free standing arcade game)
4. Myst (computer game)
5. Dungeons and Dragons (Atari 70's game)
Music (On vinyl albums)
1. Revolver - The Beatles
2. Saturday Night Fever Soundtrack - Various artists
3. Rio – Duran Duran
4. Purple Rain - Prince
5. Middle of Nowhere - Hanson
Books
1. Chariots of the Gods – Erich Von Daniken
2. Fingerprints of the Gods – Graham Hancock
3. Ninja, Invisible Assassins – Andrew Adams
4. Journey to Ixtlan – Carlos Castaneda
5. Illusions – Richard Bach
Toys
1. Major Matt Mason Lunar Command Base
2. Major Matt Mason Firebolt Space Cannon Super Action Set
3. Major Matt Mason Space Discovery Set
4. Colorforms Aliens - Alpha 7
5. Kooky Spooky Brother Mortimer Ghost
DVD Movies
1. Lemora, A Child's Tale of the Supernatural
2. Phantasm
3. The Dark
4. The Abominable Dr. Phibes
5. Batman (1966)
Comic Books
1. Avengers/Defenders Crossover (Avengers#115-118, Defenders#7-11): Everyone knows this is my favorite single comic story of all time.
2. Thor #212-216 (Sssthgar/Xorr story arc): The best Thor story ever, and my second favorite comic story!
3. Kobra #1-8: Kobra was my second favorite DC comic book after New Gods. The last issue (#8) was cancelled but printed in DC's Five Star Superhero Spectacular. It was 1 enclosed storyline, so it counts.
4. New Gods #1-19, 1st Issue Special #13, Adventure Comics #459,460: Originally I excluded the "Return" series and limited it to the original 11 issues, but it was technically the same title, and the same continuing story. So I say it should count. It's one total story, spread across several years and titles.
5. Avengers #160-171 (Ultron arc): The ultimate Ultron story!
Foods
1. Turkey with Mole sauce (Mexican dish)
2. Bharta (Indian dish)
3. Kallari 71% Dark Chocolate
4. Giordano’s Deep Dish Pizza
5. White Castle (Cheeseburgers/fries)
Good luck to whoever goes next! It's hard!
And of course, the day of the drawing my mother got a call saying we won. 
Of course, her first words were "Ok, what trick did you pull?". Parents were psychic back then. Our response? "Well, we both put in entries." Not a lie. We literally both put in entries. 
God I loved it! They have it reprinted in a graphic novel but the slick paper looks like crap. I think it's also been reprinted on regular paper. Gotta pick it up though. This was Marvel's first real major crossover, with Loki and Dormammu as villains. It was a blast!