Mr. Darden said he thought Mr. West had become “smarter and more strategic in his movements,” and Mr. West does seem increasingly aware of the multiple audiences he would like to cultivate. To wit: the “Graduation” song with the most “blatant hit-recordness,” as Mr. West called it, is “Good Life,” a relaxed, airy, radio-friendly collaboration with this year’s cameo king, T-Pain. But in a nice twist, the video for that song was directed by Mr. West’s former nemesis, So Me. The two have even been spotted together at the trendy Los Angeles dance club Cinespace. If you can’t beat them, co-opt them.

Still, Mr. West doesn’t always get it right. “I mess up so much,” he said of his forays into fashion, art and the like. He pontificated at length about some of his missteps, particularly with style. (The lavender tuxedo he wore to the 2007 Grammys is a particular sore spot.) “For me to not be on the Vanity Fair best-dressed list, it’s good,” he said. “It’s motivation. Some people are gifted at specific things, but I had to develop a certain taste level. The thing I’m most talented at is the ability to learn.”

Mr. Macklovitch has witnessed that curiosity. “I’ve seen him, in Japan, go to the bookstore and spend hundreds of dollars to learn about art or architects,” he said. “There’s kind of a naïveté there sometimes, but this guy is trying to learn about the world.”

Mr. Murakami, the artist, echoed the sentiment. “His pursuit of uncompromised detail made me feel at times like there was another me besides myself,” he said via e-mail through a translator.

Not all of Mr. West’s new reference points are so studiedly cool, though. “I’ve got to make music like a little kid,” he said of his pop instincts. “That’s what made me successful to this point.” He seeks out new musical inspiration not on BET but on VH1. The mainstream rock bands the Fray and All-American Rejects are among his favorites. He heard the snare drum he used on “I Wonder,” a song from the new album, while shopping for furniture at Moss.

“I love TV on the Radio’s production,” he said, referencing the critically acclaimed Brooklyn indie-rockers, “but man, at the end of the day, Keane and the Killers have bigger hooks.” Mr. West stops, considers, then laughs. “The last thing I need now in my quest to be cool is for somebody to think I dissed TV on the Radio.”