Lookout Records was a big influence for me growing up in the Bay Area. I was too young for the Purple Onion Budget Rock scene, but all-ages pop punk shows were abundant thanks to Lookout's support. I became a huge fan of The Groovie Ghoulies. I remember the excitement as World Contact Day came out and I went to the video shoot for Island of Pogo Pogo. Lookout also exposed me to the Hi Fives, which were the first "retro" band I ever saw. Seeing guys spazzing out with suits and vintage guitars certainly left a big impact.
What no one has mentioned so far was the change in management in 1997 and how that ruined Lookout. Larry Livermore created a defined identity for Lookout Records. With new releases, you knew that the band would fit within the style. When Livermore retired and Chris Appelgren from the PeeChees took over, it was the beginning of the end. Chris' taste was more artsy and open to emo, post-punk and more experimental groups. Gradually, the pop-punk bands were cut and different kinds of bands moved in. Part of Lookout's effectiveness was its judge of taste, but under Appelgren, you couldn't count on a band fitting into the Ramones-y pop punk idiom. I know that at the time, I quickly lost interest in Lookout and moved on to other things.