1. “When We Were Young-” “Someone Like You” is a sad song, but “Young” is much sadder. It might be an another break up song, but it’s also a song about missing your youth. The passion and the melody combined make this song a tour de force in creating a crying spell.
2. “Husbands and Wives- “This country waltz song is very sad with its melody and lyrics about the end of marriage. While Roger Miller does a great job, if you really want a good cry; listen to Brooks & Dunn’s cover of the song. They put more feeling into their take.
3. “Golden Moment-” It is a number from a lesser known stage musical called Hot December. Frank Sinatra covered the song and would eventually appear on his “My Kind of Broadway” album in 1965. When I lost my father, even this song really made me cry. As the song said, once that Golden Moment is gone, that is it. It will not come back.
4. “You Look So Good in Love-” This song from the ‘King of Country’ George Strait, has the protagonist heartbroken that he allowed his love to move on and guess what? She is going to marry this other guy. At the end Strait does brief spoken interlude about how he never saw her for who she was, and then goes into one more chorus of the song before she ties and knot and the song itself fades.
5. “Don’t Take The Girl-” This song would show that Tim McGraw was about being a romantic rather than another Country outlaw. It’s a very sad song from start to finish. It is about the love of woman that he knew since childhood and would even give up his own life for her, even if that mean he died in the hospital waiting room instead of her dying in a hospital bed. All this in spite of his father’s warning that one day, he would have to let her gosome way or somehow.
6. “Neither One of Us (Wants to Be the First to Say Goodbye)-” This song will tear jerk you from start to finish, but only if its Gladys Knight’s recording of the song. Ironically this would their final hit with Motown. Hall & Oates does a great cover of this song, but it just might not turn on the water works.
7. “Can’t Help Falling In Love-” When I was younger I did kind of cry when I heard this song. My mother always did love Elvis’s version of the song. She could never get into UB40’s reggae version of the song, which by that time she went Classical all the way.
8. “Sissy’s Song-” The song was written for Alan’s housekeeper Leslie “Sissy” Fitzgerald who was killed in a motorcycle accident 2007. He soon wrote this song and play it at her funeral. The song would be released to radio in 2009 and would peak at #9 on Billboard’s Hot Country Songs chart.
9. “Just One Person-” The finale of “Snoopy: The Musical. The second musical based on Charles M. Schulz’s comic strip Peanuts. The song talks about friendships and maybe the possibility of many more friends if only that‘one person’ steps up and takes faith in you. The song has also been associated with The Muppets since it was one of Jim Henson’s favorite songs. The song was done at Henson’s funeral with his associates doing it in character, and would be recreated for the TV special The Muppets Celebrate Jim Hensonin 1990.
10. “Seasons of Love-”Five hundred and twenty-five thousand, six hundred minutes. That is the number of total minutes in single year, and is pointed out in this song. It is a way to reflect on the fact that we are finite and some knowing first hand that their own lives will be cut short. It is an ensemble number that will make you cry, even if you don’t care for the overall musical “Rent.”