"Just a Gigolo" (Don)

"I Wish I Were A Princess" (Betty)

"September Song" (Roger/Jane)

"My Buddy" (Salvatore)

"Anything You Can Do, I Can Do Better" (Peggy)

"Let's Call The Whole Thing Off" (Lane Pryce)

"Scotch and Soda" (most of the SC executives)

"On the Outside Looking In" (Duck Phillips)

"You're Havin' My Baby" (Pete Campbell)

"Mr. Big Stuff" (Pete Campbell)

"My Guy" (Salvatore Romano)

"Everybody Loves Somebody Sometime" (Don)

Sal: "The Great Pretender" (Actually, pertains to most of the cast characters!) This is a great thread!

@Rasputin and Egypt. Great stuff! Here’s my take:

Don: If I’m not with the girl I love, I love the girl I’m with
Betty: Hard-hearted Hannah
Peggy: I’ll take Manhattan
Joan: See the gal with the red dress on, she can do the shimmy all night long
Roger: The September of my Years
Sal: Can’t we be friends
Bobbi Barrett: She’s a Man-Eater
Jimmy Barrett: Pagliacci
Jane: Oh Daddy, I want a diamond ring, bracelets, everything
Freddie: What did I do? What in the world did I do?
Duck: That’s life!

@Fifty-Two: Thanks for the great thread! Your choices were terrific too!

@Drink and Sandy: Your choices were wonderful too.

Another Don-ism: I'm Old Fashioned (with a double Rye).

Another Joan-ism: Big girls don't cry

Mad Men the Musical?

"The Lady is a Tramp" (Bobbie Barrett)
The Supremes' "Love Child" (Peggy)
Billy Joel's "Only the Good Die Young" (Peggy)
Sinatra's "Strangers in the Night" (Betty's pickup last season)
Sinatra's "Call Me Irresponsible" (Don)
CSN&Y's "Love the One You're With" (Don and selected cast members)
Sinatra's "Drinking Again" (Entire Cast)
Dylan's "Positively 4th Street" (Jeffrey and Paul)
The Who's "Squeezebox" (Joan)
Peaches & Herb's "Shake Your Groove Thing" (Joan)
The Platters' "Smoke Gets In Your Eyes" (Entire Cast)
Simon & Garfunkel's "Mrs. Robinson" (Betty and Glenn)
"I Get Around" (Title Only, Don)
The Silhouettes' "Get a Job" (Duck Phillips)

"Walk Like a Man" (Salvatore)

Jimmy Buffett's "Why Don't We Get Drunk (and S****)" (Don, Pete, Roger...)

Yay! You people are fun, fun, fun! Here's some more:

Don't You Forget About Me (Bobby)
Love for Sale (Vicky)
Hey There Lonely Boy (Ken)
Peg 'o My Heart (Smitty)
Walk Right In (Glenn)
This Diamond Ring (guess who?)
Hurt So Good (guess who?)

"Great Balls of Fire" (Don and Roger)
"I Get Around" (Peggy)
"My Cup Runneth Over" (Joan)
"Hotel California" and "California Dreaming" (Joy and the Jet Set Group)
"My Boyfriend's Back" (Sal Romano)
"Should've Said No" (Kitty Romano)
"Are You Lonesome Tonight?" (Ken Cosgrove)
"Footloose" (Bert Cooper)
"Strangers in the Night" (Most Sterling Cooper Employees)

Duck: How Much is that Doggie in the Window?

Go Away Little Girl (Betty)
Stand by Your Man (Trudy)
Big Hunk O' Love (Joan)
Liar Liar (Don)
These Boots Are Made for Walking (Sally)
Take Good Care of My Baby (Peggy)
Our Day Will Come (Carla)

I forgot this one last night. The song really exists.

"Hey, Bellboy!" (SAL)

Someone to Watch Over Me (Chauncy)

@Cattychick: WOW. I remember that song but don't remember who performed it. Wasn't it mostly an instrumental and the periodic words "Hey Bellboy" shouted out?

@Cattychick: I just remember who performed "Hey Bellboy." It was Pete Candoli (a side man with Stan Kenton) and vocals by Gloria Wood.

Well, I'm a Beatles freak, so here goes...these are either about the character or their song

Bert Cooper: "Old Brown Shoe" or "Octopus's Garden"
Roger: " Help"
Don: "Hard Days Night"
Betty: "Oh Girl"
Peggy: "Norwegian Wood"
Joan: "Something"
Pete: "You Never Give Me Your Money"
Ken: "Paperback Writer"
Paul: "Revolution"
Harry: "Baby You're A Rich Man"
Jane: "Day Tripper"
Sal: "Carry That Weight"

To the whole Mad Men cast: "All You Need Is Love"

Sorry I haven't been listing the original artists on my choices. I can supply them if anybody wants 'em.

Baby the Rain Must Fall (Freddy)
Itsy Bitsy Teenie Weenie Yellow Polkadot Bikini (Betsy)
Wedding Bell Blues (Roger's Daughter)
The Happy Organ (Don)
Barefootin' (Bert C.)
I Can't Get Next to You (Kitty)
Mama Told Me Not to Come (Pete)
Will You Still Love Me Tomorrow? (Shelley)
Hanky Panky (Everyone at SC)
Daddy Don't You Walk So Fast (Bobby and Sally)

"Wives and Lovers" (Don, Pete, Roger)
"September in the Rain" (Freddy Rumsen)

"Come Back When You Grow Up" (Peggy)

"Lay Lady Lay" (Don, Pete, Roger)

Sorry, I send in one and then think of two more!

"Shake Your Groove Thing" (Joan)

The Mills Brothers' "Enjoy Yourself (It's Later Than You Think)" (Roger)

I have been working on mix that would have Don's relationships with the women in his life. I am debating whether or not Betty and Peggy should have different songs for each season as the relationships change so much.

Midge - "Sidedish Friend " Rachael Yamagata
Peggy - "Daybreaker" Beth Orton (More S2 than S1)
Rachael - "Hysteric" Yeah Yeah Yeahs
Betty - "Asking for Flowers" Kathleen Edwards (again more S2 than S1)
Joy - "Easy" Emiliana Torrini

From "This is Spinal Tap": "Big Bottom" (Joan)

Don: Tom Sawyer, Rush
Betty: I Wanna Be Sedated, The Ramones
Pete: Tequila, The Champs
Freddie: One Bourbon, One Scotch, One Beer, George Thorogood & the Destroyers
Sal: Take a Walk on the Wild Side, Lou Reed
Dr. Greg Harris, Date Rape, Sublime
Vicki: Roxanne, The Police
Bobbie Barrett: December, Collective Soul
Mona Sterling: You Oughta Know, Alanis Morissette
Glen: Only a Lad, Oingo Boingo
Sally: Sheena is a Punk Rocker, The Ramones & I Don't Like Mondays, The Boomtown Rats

In 1960 The Fantasticks! opened at the Sullivan St. Playhouse in Greenwich Village. It remained a big hit until 2002. From it:
For Bert Cooper: Try to Remember a Kind of September.
For Greg Harris: The Price You Pay, often called "The Rape Song" also from The Fantasticks!
For Joan: Always True To You, Darling, In My Fashion from Kiss Me Kate
For Freddy Rumsen: Anything Goes
For Gene Hofstadt: When Johnny Comes Marching Home
For Roger: Don't Sit Under the Apple Tree
For Dick/Don: You're In The Army Now!
For Peggy: I Believe In You from How to Succeed in Business Without Really Trying
For Sal: The Land Of Might-Have-Been by Ivor Novello
For Trudy: Why Isn't It You?
For Jane: Diamonds Are A Girl's Best Friend
For Kitty: Gonna Wash That Man Right Out Of My Hair
For Ken: Let's Misbehave
Hildy: Easy To Love by Cole Porter

Joy: Super Freak, Rick James
Joan: Baby's Got Back, Sir-Mix-A-Lot
Rachel: Never Gonna Get It, En Vogue

"My Rifle, My Pony and Me" (Betty)