OMG it's crazy how much I dig Erin Esurance, the animated mascot who appeared in tons of commercials between 2004 and 2010. I made a gallery once, though I may delete it someday. (Or not.) Anyway, I've made a playlist of as many of Erin's ads as I could find on YouTube (32, for now, though you never know when some of them might stop working; note that the first video on the list will only play on YouTube, not on this page). I also found a couple of 2009 Star Trek tie-in ads, on Filmsnmovies.com. So I've included them here (though I wish I could find them on YouTube).
I'm disappointed that they eventually stopped making ads with Erin, but in 2013 there was a funny ad that ties in with the movie Star Trek Into Darkness. It's probably the best non-Erin ad I've ever seen for Esurance. So, I've added it to the playlist. I also added a 2014 ad, "Beatrice," just because the line "That's not how it works! That's not how any of this works!" has become online meme-fodder, which is kind of fun.
Meanwhile, there are some Erin Esurance ads that I haven't been able to find anywhere online, but there are some sites where you can see some ads that aren't on my YouTube playlist (as well as some that are), including Ghostbot and Special Agent Productions.