2023 Valentine’s Day 50 Greatest Love Songs Countdown
Every year here at MITM, we ask for you tell us what you think are the greatest love songs of all time. It’s not hard to think of romantic songs as we play them all the time. The hard part comes from figuring out how to choose a favorite.
The votes are in for our 16th annual Valentine’s Day 50 Greatest Love Songs Countdown poll. Did your favorite song make the list? Thank you for voting!
| Rank | Title | Artist |
| 1 | How I Will Say I Love You | Tony DeSare |
| 2 | When I Fall in Love | Nat King Cole |
| 3 | The Way You Look Tonight | Steve Tyrell |
| 4 | At Last | Etta James |
| 5 | Fly Me to the Moon | Frank Sinatra |
| 6 | Isn’t It Romantic | Diana Krall |
| 7 | All the Way | Frank Sinatra |
| 8 | This Love of Mine | Michael Buble’ |
| 9 | You Belong to Me | Jo Stafford |
| 10 | Taking a Chance on Love | Renee Olstead |
| 11 | Sway | Dean Martin |
| 12 | Unforgettable | Nat King Cole |
| 13 | This Guy’s in Love | Steve Tyrell |
| 14 | Fever | Peggy Lee |
| 15 | What Are You Doing the Rest of Your Life | Chris Botti and Sting |
| 16 | Love is Here to Stay | Ray Charles |
| 17 | Come Rain or Come Shine | Frank Sinatra |
| 18 | We Are in Love | Harry Connick Jr |
| 19 | Never Never Never | Renee Olstead and Patrizio Buanne |
| 20 | I’m Your Man | Michael Buble |
| 21 | Everybody Loves Somebody | Dean Martin |
| 22 | Night and Day | Frank Sinatra |
| 23 | For Once in My Life | Tony Bennett and Stevie Wonder |
| 24 | My Funny Valentine | Chet Baker |
| 25 | I Love You | Frank Sinatra |
| 26 | At Long Last Love | Nancy Wilson |
| 27 | My Valentine | Michael Buble |
| 28 | That’s All | Mel Torme |
| 29 | Besame Mucho | Jane Monheit |
| 30 | Cheek to Cheek | Tony Bennett and Lady Gaga |
| 31 | Let There Be Love | Nat King Cole |
| 32 | Haven’t Met You Yet | Michael Buble |
| 33 | Let’s Fall in Love | Diana Krall |
| 34 | Everything | Michael Buble |
| 35 | Strangers in the Night | Frank Sinatra |
| 36 | Last First Kiss | Tony DeSare |
| 37 | Moon River | Andy Williams |
| 38 | All or Nothing At All | Frank Sinatra |
| 39 | Be My Valentine | Jonny Blu |
| 40 | The Nearness of You | Norah Jones |
| 41 | L-O-V-E (bi-lingual version) | Nat King Cole |
| 42 | Someone to Watch Over Me | Renee Olstead |
| 43 | Bewitched, Bothered and Bewildered | Steve Tyrell |
| 44 | The Very Thought of You | Chris Botti and Paula Cole |
| 45 | In The Wee Small Hours | Frank Sinatra |
| 46 | Besame Mucho | Andrea Bocelli and Natalie Cole |
| 47 | Bella Notte | Steve Tyrell |
| 48 | You Will Be My Music | Frank Sinatra |
| 49 | I’m In The Mood For Love | Steve Tyrell |
| 50 | A Bushel and a Peck | Doris Day |