Jeffrey Zeldman has a blog post entitled Web 2.0 Thinking Game where he writes

A few weeks back, The Economist was calling “Web 2.0″ a trend. Their phrase was, “hot Web 2.0 trend.” The magazine now intends “Web 2.0″ to be understood as a sort of second edition:

This week’s pairing of Google and YouTube may come to be remembered as the moment “Web 2.0″—ie, the web, version two—came of age.

Clearly “Web 2.0″ means different things to different journalists on different days. Mostly it means nothing—except a bigger paycheck. But let’s simplify what The Economist is saying:

Web 1.0: AOL buys Time Warner.
Web 2.0: Google buys YouTube.

Put another way:

Web 1.0: New media company buys old media company.
Web 2.0: New media company buys new media company.

If we’re stuck with this meaningless Web 2.0 label, let’s at least have some fun with it. Here’s my new game. I’ll start, you finish:
...
Web 1.0: Users create the content (Slashdot).
Web 2.0: Users create the content (Flickr).

Web 1.0: Crap sites on Geocities.
Web 2.0: Crap sites on MySpace.
...
Web 1.0: Karma Points.
Web 2.0: Diggs.

Web 1.0: Cool Site of the Day.
Web 2.0: Technorati.com.
...
Now you try it!

There are a lot of funny ones in the comments as well such as

Web 1.0: Old folks have no clue.
Web 2.0: My parents just left a comment on my blog. - Charlie

Web 1.0: Rational Unified Process implementing J2EE
Web 2.0: “Getting Real” using RoR - Kevan Emmot

Web 1.0: 20,000 Hits on my webpage!
Web 2.0: Ive been dugg 1000 times on Digg! - Regnard Raquedan

Web 1.0: Pamela Anderson
Web 2.0: Paris Hilton - Chase

Here're a couple of my own, let's see what you guys come up with

1. Web 1.0: Netscape IPO
   Web 2.0: Google IPO
   

2. Web 1.0: My startup just IPOed, I'm gonna be rich
   Web 2.0: My startup just got bought by Google, I'm gonna be rich

3. Web 1.0: Napster
   Web 2.0: YouTube
   

4. Web 1.0: Yahoo! Bookmarks
   Web 2.0: del.icio.us
   

5. Web 1.0: Java applets
   Web 2.0: Widgets
   

6. Web 1.0: Beth Goza
   Web 2.0: Niniane Wang