1. Frank Sinatra, "My Way"
"My Way" has never been my favorite Sinatra song by a long shot, but there's no denying that Frank consistently ripped the sky open with his live performances of this Paul Anka setting of the French song "Comme d'habitude." After a Florida dinner with Frank and some of his heavies at which Sinatra told Anka "I'm quitting the business. I'm sick of it. I'm getting the hell out," Anka wrote the song from his imagined version of Frank's point of view. Sinatra recorded it in 1968, and it became an instant classic and a crown jewel in his repertoire. You've been marvelous, absolutely marvelous. Now get the hell out of my house!
2. Sarah Brightman/Andrea Bocelli, "Time to Say Goodbye"
Sarah Brightman and Andrea Bocelli are two of the largest stars in the genre known as "classical crossover." Bocelli is the biggest-selling singer in the history of classical music, which I imagine keeps Luciano Pavarotti up at night concocting elaborate revenge fantasies. This is an English-language version of Bocelli's biggest hit, "Con te partirņ," which is most memorable to me for having been used as Carmela Soprano's recurring theme song. A great choice for those whose wills request that when they die they be buried inside Satriale's Pork Store.
Best YouTube Comment: "My favorite kinds of music are dubstep, oldschool punk, emo rock, and alternative…but dude…THIS SONG DUDE!!!" —TheOrigGearhead
3. Bette Midler, "Wind Beneath My Wings"
A shining testament to the world before Auto-Tune.
Best YouTube Comment: "After 7 years of mums passing it still makes me cry like a sobbing girl. Miss mum so much." —Sleipner77
4. Eva Cassidy, "Over the Rainbow"
Washington, D.C., area singer and guitarist Eva Cassidy passed away in 1996, but four years later her cover of "Over the Rainbow" became a surprise hit in the U.K. (and later worldwide) after Terry Wogan played it on BBC Radio 2. Cassidy subsequently became a posthumous musical sensation, and her arrangement of "Over the Rainbow" is now a staple on televised singing competitions.
Best YouTube Comment: "Hey there, this exact version was also played at my granny's funeral…I miss her a lot…I guess the song does bring back memories" —gunblade86
5. Robbie Williams, "Angels"
The sound of Robbie Williams high-fiving a million angels. And none for the Jessica Simpson version, bye!
Best YouTube Comment: "This Was Played At My Grandads Funeral It Will Always Stay With Me" —JackCoolDude
6. Westlife, "You Raise Me Up"
Wikipedia calls this song "a popular song in the inspirational mould" (yes, we said "mould" — Westlife are British). It was actually an instrumental at first, interpolating Irish classic "Danny Boy," which is itself a version of folk tune "Londonderry Air." Americans are probably more familiar with the version of "You Raise Me Up" by Josh Groban. All told, this song sounds a lot like "The Wind Beneath My Wings" but not nearly as good. This is your future, One Direction!
Best YouTube Comment: "the very essence of life, when we are a stronghold to our neighbor, we show that humanity and love is real!" —MrLuky3000
7. Gerry and the Pacemakers, "You'll Never Walk Alone"
Somehow this tearjerker from Rodgers and Hammerstein's Carousel became the favored theme song of British football clubs, starting with Liverpool in the early '60s. Pink Floyd sampled a Liverpool stadium crowd singing it for "Fearless" on their 1971 album Meddle. (It is also the memorial song for the Hillsborough disaster.) "You'll Never Walk Alone" is powerfully simple and endlessly durable, tho' your dreams be tossed and blown. Oh great, now I'm crying. Thanks a lot, Gerry and the Pacemakers!
Best YouTube Comment: "This song was very important to my dear husband who died one year ago today and it was played at his funeral as requested by him before he died. I have posted this video on Facebook in his memory…" —gismogannie
8. Vera Lynn, "We'll Meet Again"
An optimistic World War II–era anthem that modern audiences probably know mostly from its use in the final scene of Stanley Kubrick's Dr. Strangelove. The Pink Floyd song "Vera" from The Wall is about Vera Lynn, who became known as "The Forces' Sweetheart" for her popular sentimental songs during WWII. Those Pink Floyd lads sure do love their English history and culture. "We'll Meet Again" has been covered by Johnny Cash, The Byrds, and the Turtles, but Lynn's haunting version is still the best. In 2009 she became the oldest living artist to rank at no. 1 on the British album chart, at the age of 92. Carry on!
Best YouTube Comment: I was just 8 years old when the war started, and just discovered this Video.’ Thank you for posting it —John Mason from Brooklyn NY USA
9. Celine Dion, "My Heart Will Go On"
Kate Winslet has admitted that the Titanic theme song made famous by the French-Canadian diva makes Winslet "feel like throwing up." We know the feeling!
Best YouTube Comment: "First time I listen to this: I cried oh so very badly, Second: my heart cried, Third: my heart died, Fourth: my heart filled with pain and sorrow and I thought about love, Fifth: I thought about the Titanic and spent 1 hour in my room thinking about it. * goes on to 100 WHEN YOUR HEART TELLS YOU TO CRY, TELL IT YOU HAVE A MILLION REASONS TO SMILE. This song does both." —justisine
10. Nat King Cole, "Unforgettable"
This is for the part of the funeral when everyone takes turns singing duets with a hologram projection of the deceased.
Best YouTube Comment: "this song no matter how old will withstand the test of time as one of the classics." —ShiftingPurple