Over the last year, I have flirted with two separate lunchboxes, evaluating both on a series of criteria specific to my diet, transportation, aesthetic, and otherwise picky needs. The following is my evaluation, prepared here for your reading pleasure and general dining edification:

Contestant #1: Mr. Bento
Cost: $39.99 from Amazon, prices may vary in retail stores
Description: More of a traditional Bento box, Mr Bento contains four inner containers in an outer bullet-like case.
Interior containers: Four plastic containers in total, two with snap-on lids (like Tupperware), one with a screw-on air seal lid, and one with a screw-on thermal lid. Four slightly different sizes of containers.
Exterior/carry case: Metal/metallic thermos-like container with plastic lid that snaps on with side hinges. Canvas-like carry-case with handle and/or shoulder strap.
Amenities: Comes with either chopsticks (in their own hinged hard plastic case) or spork (with cover).
Sample meals: Mr Bento Porn Flickr Group (totally SFW)

Contestant #2: Laptop Lunchbox
Cost: $20.99 for the most basic model from Laptop Lunches, fancier models come with more but also cost extra
Description: Brightly-colored plastic hinged lunchbox with modular internal containers.
Interior containers: Five hard plastic containers in a variety of sizes. Two containers (3x5x2 and 2×1.5×2) have lids, the rest are open.
Exterior/carry case: Hard plastic hinged container. No handle or carry case.
Amenities: Comes with silverware and a cookbook with suggestions on packing healthy meals.
Sample meals: Laptop Lunches Flickr Group

Things I like about Mr. Bento:

• The thermal lidded container does a good job of keeping cold things cold. It doesn’t keep frozen things frozen, but that’s asking a bit much.
• The air-seal lidded container does a very good job of keeping liquidy things from leaking. I never once had a spill from my lunchbox when carrying Mr. Bento.
• The carry-case is very nice and has extra room for things like napkins or teabags or packets of things that didn’t fit in the container itself.
• Lots of little containers meant that I put a lot of thought into packing my lunch.

Things I dislike about Mr. Bento:

• Honestly, it’s pretty bulky. If you don’t carry much back and forth to work, or if you drive, this probably isn’t an issue, but it was frustrating when I was commuting on my bike with my laptop and an assortment of other things. Mr. Bento just didn’t fit in my bag very well. If your workplace has limited fridge space, this could be an issue as well.
• On the one hand, packing my lunch into lots of little containers was fun and made me think about what I was eating. On the other hand, because it doesn’t make sense to pack the Bento WITHOUT all the internal ones, I felt like I was packing more food than I really needed.
• Things larger than a bagel (or something with bagel-like dimensions) – a slice of leftover pizza, a bag of chips, an apple – don’t fit, and there’s no good way of making them fit short of cutting them up and/or otherwise changing their original dimensions.

Things I like about the Laptop Lunchbox:

• The bright colors appeal to my inner 7 year old.
• The containers are, on the whole, smaller than Mr. Bento’s, so it’s better for portion control.
• You can remove all of the internal containers and still use the lunchbox – so, for example, if you wanted to take a slice of pizza, you could take out two containers, put in the slice of pizza, and still use the remaining containers. Alternately, you could take out all the containers and fill the box up with a big salad or something.
• The entire package is more compact, so it fits well in my small messenger bag along with my wallet, book, iPod, and other commuting essentials. It also fits nicely in the compact office fridge.
• It’s easy to buy extra accessories like a thermal sleeve, a carry case, a matching thermos, replacement containers, etc.

Things I dislike about the Laptop Lunchbox:

• The lack of lids can be a problem. The provided lids are very good, but what if you want to bring yogurt AND granola and don’t want the granola getting everywhere? I’ve been using Press’n Seal (what kind of a silly name is that?) wrap, and up until today have had no problems, even with soup! Today, however, I had leaky beans, but the damage was minimal. Even with Press’n Seal, you’re potentially pushing your luck, so I’ve been double extra cautious (again, up until today) and have put the lunchbox in a plastic bag in my bag for transportation purposes.
• No thermal powers whatsoever. This hasn’t been an issue as I haven’t had to take it anywhere without access to a fridge, and this problem could be remedied with the purchase of the thermal sleeve or insulated carry case, available for about $15 each.

Overall, for my purposes the Laptop Lunchbox is the winner. It is compact, the portions are smaller, and I feel like a little kid every time I pack my purple (!) lunchbox with rainbow colored containers. I imagine there will be instances when I still use Mr. Bento, but for the most part, my needs are met by the Laptop Lunchbox. For the price of Mr. Bento ($39.99), you could buy the entire Laptop Lunchbox system (lunchbox, containers, silverware, cookbook, insulated carry case, and water bottle) ($34.99) – or you could save $15 and get the basic model.

I invite discussion on this important topic.