A Vintage Playlist To Win Friends And Influence People (or at least drown out awkward moments)

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Music should be the last thing you worry about when you’re having a gathering at your place. Dropping the apple pie you baked? Running out of alcohol? Someone showing up with the ex-boyfriend of another guest? Yes, worry about those things, but let us handle setting the mood for you by suggesting 24 songs with a vibe that oozes vintage-y cool. 

I (Lara) think this playlist works well when you’re having a casual get-together where you’re just kind of hanging out, having drinks and snacks, and catching up with everyone. You can mix these songs up, or just play them in this order, as I’ve balanced everything out and taken into account the male to female ratio and tempo and newer versus classic artists to keep things interesting.

Pro Tip: Make your selection POP by mixing in live versions of favorites, random cover versions, remixes, and instrumental versions. All of these add a certain “texture” that can break up the sameness that tend to kind of lull people into a stupor and make a function low-energy. And unless I’m on the couch with a bag of Dulse Chips and an Ava Gardner movie marathon on TCM, I’d rather be stupor-free.

Pro Tip, Part Deux: My friend Brad Martini Chambers is the Morning Man and owner of www.MartiniInTheMorning.com, which plays Standards 24/7 (including all the songs on this playlist), so he lives and breathes the Lounge Lizard lifestyle. Brad says you can never go wrong by including Frank Sinatra and Ray Charles, even if you’re focusing on more current pop hits. Frank and Ray are so genius that they will even sound cool next to Gaga, Rihanna, and Maroon 5, and your friends will admire your stellar taste and knowledge in music. Brad also says that, when in doubt or short on time, just put on Frank’s In The Wee Small Hours album (and get ready for love) or Songs For Swingin’ Lovers (and get ready for love) and let them roll all the way through.

Without any further ado, here’s the list:

1. Norah Jones / The Nearness of You: “It’s not the pale moon that excites me, That thrills and delights me…”  The moment you hear Norah’s voice you can let out a huge sigh, allow your shoulders to drop down from around your ears, and know that life is about to get much, much better.

2. Frank Sinatra / I’ve Got You Under My Skin: I’ve got the horn section under my skin. I fantasize about the moment it kicks in at 2:05. And then Frank comes back in to sing about sacrificing everything just to have me near. I want to weep. And you will, too, when you listen to it LOUD.

3. Michael Buble and Sharon Jones / Baby (You’ve Got What It Takes): This was first done as a duet with Brook Benton and Dinah Washington, and Michael and Sharon do a fabulous job following in those awesome footsteps. Michael is married to an actress, btw, and says that, since they are apart so much, they have many dates via skype. Oh, to be a fly on the wall…

4. Peggy Lee / Fever: Often imitated, never duplicated…this is the real thing, baby. You will need some water for yourself and your guests to cool down while listening to Miss Peggy. Reese Witherspoon is playing her in an upcoming biopic.

5. Michael Feinstein / Begin The Beguine: Michael recorded this song as part of The Sinatra Project in 2008. While the album is a tribute to Frank, Michael interpreted the songs a little differently than The Chairman did, and the result is beautiful and brilliant.

6. Dean Martin / Ain’t That A Kick In The Head: “Live, direct from the bar – Dean Martin!” The most lovable drunk ever…who wasn’t really a drunk. Was it Ginger Ale in his ever-present glass?

7. Joseph Leo Bwarie / Umbrella / A Fella With An Umbrella: What happens when you combine an Irving Berlin tune from Easter Parade…with Rihanna? MAGIC…ella ella eh eh eh!

8. Ella Fitzgerald / The Lady Is A Tramp: The first lady of song. Need I say more?

9. Seth MacFarlane and Sara Bareilles / Love Won’t Let You Get Away: That’s right, the Family Guy guy can also sing. Is there anything this man cannot do? I wish I could be there to see your jaw hit the floor when you hear him—he has an amazing style and sound in the tradition of Frank and Dino. This is a cute song originally done by Bing Crosby and George Clooney’s Aunt Rosemary.

10. Nina Simone / My Baby Just Cares For Me: It was written in 1930, Nina recorded it in 1958 for her debut album, and it became a huge hit in 1987 when Chanel used it in a perfume commercial. It became Nina's signature song.

11. Steve Tyrell / The Way You Look Tonight: Yes, Steve Martin was hi-larious in Father of the Bride, but I think Steve Tyrell’s version of this classic stole the show. It never, ever gets old. If you want your woman to do anything for you, play her this song while gazing into her eyes.

12. Sammy Davis Jr. / Come Rain Or Come Shine: At some point, I am going to put together a baby making music playlist, and Come Rain Or Come Shine is probably going to be at the top of this list. This is a great one for weddings, too.

13. Bobby Darin / Mack The Knife (live version from his tv show): I’m still not sure exactly what this song is about (does someone die?), or who Ol’ Lucy Brown is, but just try to resist belting it out while snapping your fingers Darin-style.

14. Nikki Yanofsky / Sunny Side Of The Street / Fool In The Rain: Nikki was only 15 (she’s 18 now) when she came up with the idea to put a Jimmy McHugh song together with a Led Zeppelin tune. Thank you, Ma and Pa Yanofsky, for being classic rock fans.

15. Ray Charles / Hallelujah I Love Her So: Blues, gospel, and jazz—Ray combined them all and shook up pop music with a unique sound in the mid-50s.

16. Rod Stewart / Moon River: Rod the Bod had lots of pop hits (who can forget Love Touch from the movie Legal Eagles? Not me!), but his greatest success has come with recording The Great American Songbook. His cover of Henry Mancini and Johnny Mercer’s tearjerker is on Volume V!!!!

17. Kevin Spacey / Hello, Young Lovers: Ever since he did the movie Beyond the Sea, all I see is Bobby Darin when I look at Kevin Spacey. And when I see Bobby Darin, I think it is Kevin Spacey.  This version MOVES!

18. Carly Simon / Ev’ry Time We Say Goodbye: Carly is so sultry on this Cole Porter tune, I am wondering why anyone (Warren Beatty?) has ever said goodbye to her. There’s no love song finer…but how how strange the change from major to minor…

19. Chris Isaak / Besame Mucho: The title roughly translates to “Kiss Me A Lot,” which is what one of my friends who dated Chris back in the day got to do. My favorite story she told me about him is this one: One day when they were hanging out at his house, Chris came up to her and said, “I’m the thinkin’ police. Whatcha thinkin’?” Hopefully, her answer was, "Besame mucho."

20. Tony Bennett / Don’t Get Around Much Anymore: Tony is 86 with a HOT career! He’s going to be doing a third Duets album, and this time he’ll be paired with Latin artists. Gloria Estefan, that means YOU. Hey, maybe they’ll do a lounge version of Conga?

21. Chris Botti and Steven Tyler / Smile: Take a trumpet player who has been called the hardest working man in the jazz business and team him up with the surprisingly sweet (as we found out on American Idol) lead singer of Aersosmith and you have tender, beautiful tune.  I’ve heard that Smile was Michael Jackson’s favorite song. 

22. Judy Garland / Zing! Went The Strings Of My Heart: If all you know of Judy Garland is Toto, Ruby Red Slippers, and Over the Rainbow, you are missing out, sister. She sang this in a film called Listen, Darling (1938), which actually came out a year before The Wizard of Oz.

23. Frank Sinatra / Summer Wind: If you have ever loved and lost (and as they say, the only love that lasts is the one that’s not returned), this song will haunt you. I always wonder if maybe he was thinking about Ava Gardner as he sang? Surprisingly, Wayne Newton recorded this first, but Frank’s version (1966) was the bigger hit. I look for this on every jukebox I come across—it’s always a crowd-pleaser.

24. Jane Monheit  / The Rainbow Connection: You cried when Kermit sang it as a child, and now prepare for tears as you hear Jane’s gorgeous grown up version. Something tells me she has always loved this song, as she got the title of the album it’s on from a lyric: The Lovers, The Dreamers, and Me.