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A hotel renovation uncovers the remains of a young woman named Ally Thurston who disappeared in 1960. She had become an airline stewardess that year with dreams of seeing the world, but was quickly sobered by the rampant sexism and harassment she had to endure. Meanwhile, Lilly finally comes into contact with the mysterious Paul Cooper.
- Kathryn Morris as Lilly Rush
- Danny Pino as Scotty Valens
- John Finn as John Stillman
- Jeremy Ratchford as Nick Vera
- Thom Barry as Will Jeffries
- Tracie Thoms as Kat Miller
- Amanda Schull as Ally Thurston
- Lee Majors as Dean London (2008)
- Adrienne Barbeau as Dr. Helen McCormick (2008)
- Megan Boone as Helen McCormick (1960)
- Lindy Booth as Gloria Flagstone (1960)
- Robb Derringer as Capt. Rowland Hughes (1960)
- David Giuntoli as Dean London (1960)
- Brett Halsey as Rowland Hughes (2008)
- Mariette Hartley as Gloria Flagstone (2008)
- Art LaFleur as Bert Walters (2008)
- John O'Leary as Lew Thurston
- Craig Braun as Harvey Dwight (2008)
- Zach Lewis as Bert Walters (1960)
- Steven Adam Ellison as Harvey Dwight (1960)
- Leon Simmons, Jr. as Chess Opponent
- Kelsey Lewis as Girl
- First appearance of Raymond J. Barry as Lilly's estranged father Paul Cooper, though he was previously seen in a picture in "Triple Threat".
All songs are perfomed by Frank Sinatra
- Come Fly With Me
- Too Marvelous For Words
- I've Got the World on a String
- Little Girl Blue
- Closing Song: Someone to Watch Over Me