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Following the album's success, Laswell signed to Vanguard Records, and then recorded and released his second studio album Through Toledo in July 2006.
The album was written during Laswell's divorce from his wife; he stated: "It's basically a breakup album..the biggest surprise has been when you resurface out of the dark little studio.
It has nothing to do with anything that I originally wrote about. I'm just lucky to be in the loop." In spring 2008, Laswell joined the European leg of the Hotel Cafe Tour, hosted by Tom Mc Rae.He released an EP titled How the Day Sounds in March 2008, which preceded his third studio album Three Flights from Alto Nido, released in July.Several songs from the album, including "Comes and Goes (In Waves)", "How the Day Sounds" (which features Elijah Wood in the music video), "Sweet Dream", and "And Then You" have been featured in the television shows like Grey's Anatomy, True Blood, Castle, 90210, Army Wives and Dollhouse.Michaelson performed "Sally's Song" from at the event, which honored the Oscar-nominated composer.Prior to the big show, Michaelson, 35, arrived in character as Sally and happily walked the red carpet arm in arm with actor and singer Chase, 44.