A few months ago I discovered Gil Fronsdal, a Buddhist scholar and teacher whose explorations of Vipassana and Zen led him to study in monasteries throughout Asia and also to Stanford University. Gil’s dharma talks are posted on the Web and are amazingly digestible and thought-provoking for a novice Westerner.
There are almost 500 of his talks posted for free download. His own selection of best 32 talks--in order--are at www.audiodharma.org/talks-rec.html. I'm about half way through; I took him backpacking with me a few months ago. There's also a site called Zencast that mixes talks by Gil and others with some music and also classic talks by people like Shunryu Suzuki.
"Gil has practiced Zen and Vipassana since 1975 and has a Ph.D. in Buddhist Studies from Stanford. He has trained in both the Japanese Soto Zen tradition and the Insight Meditation lineage of Theravada Buddhism of Southeast Asia. Gil was trained as a Vipassana teacher by Jack Kornfield and is part of the Vipassana teachers' collective at Spirit Rock Meditation Center. He was ordained as a Soto Zen priest at the San Francisco Zen Center in 1982, and in 1995 he received Dharma Transmission from Mel Weitsman, the abbot of the Berkeley Zen Center. He has been the primary teacher for the Insight Meditation Center in Redwood City, California since 1990. He is a husband and father of two boys."