Live With Regis and Kelly 20th Anniversary
What: Kathie Lee Gifford returns to her former talk show to celebrate its 20th season with Regis Philbin.
When: Sept. 14
Highlights: Kelly Ripa has nothing to worry about – Kathie Lee's just visiting! After leaving her post in 2000 – to spend time with her family and write – Gifford caps off a two-week anniversary celebration by visiting her former talk show. And after seven years, an update about Cody is, uh, long overdue.
Curb Your Enthusiasm
What: Larry David is up to all his uncomfortable hijinks as season 6 begins
When: Sept. 9, 10 p.m. on HBO
Highlights: After a two-year hiatus, the popular HBO comedy is back, boasting its characteristic blend of painful humor, now with a stormy twist: David's character takes in hurricane victims!
What: Dave Matthews, Counting Crows, Neil Young and others rock out at the annual festival, held this year at Randall's Island in New York
When: Sept. 9, 12 p.m.
Highlights: It's the 22nd anniversary of Willie Nelson's annual benefit concert – which raises money for family farmers. Expect lots of collaborations, duets and YouTube-worthy musical moments.
Brian Ach / WireImage; Jim Spellman / WireImage
Kanye West vs 50 Cent
What: What happens when two megastar rappers release their anticipated albums (West's Graduation and 50 Cent's Curtis) on the same day?
When: In stores Sept. 11
Highlights: There's already been plenty of (faux) drama after 50 Cent claimed that if West's record outsold his, he would retire from his solo career. Neither seem too serious (and they performed together onstage in New York), but you never know. West recently told PEOPLE, "I wish he wouldn't [retire] because he's one of my favorite rappers."