When the iPhone was announced in 2007, they realized that on-screen keyboards and multi-touch control were the future, so they did a complete redesign, moving to an interface similar to the iPhone. Here's a quote from one of their engineers talking about the iPhone announcement:
“As a consumer I was blown away. I wanted [an iPhone] immediately. But as a Google engineer I thought ‘We’re going to have to start over’” Chris DeSalvo said. “What we had suddenly looked so… nineties. It’s just one of those things that are obvious when you see it.”
[Every time this story is told, I like to remind - note how fast Google were able to pivot / adapt when Microsoft with their crazy resources and Engineering might took way longer. (Even beyond that MS had to change the way apps were developed for WP.) Fact is Google/Danger/Android were in a fundamentally good position mobile OS design wise way before the iPhone. After the iPhone - they looked at the possibilities of multi touch soft keyboard UI and were able to get there and surpass fairly fast.]
But even adjusting for that it took MS 3-4 years after the iPhone to just get Windows Phone 7 out, and that was also clearly a rushed release, because they had to throw everything out for Windows Phone 8.
They were the first to do push based email and IM in a context outside of business AFAIK.
I believe after rage from Jobs they left out multitouch zooming at first and did something double tap based, even though MS had done it before Apple (without capacitive) and Minority Report has shown it.