“Last Kiss,” Snickers, and I think it was Pearl Jam.
Oh, how I love bad songs. There are some wonderful gems in here. I think I smell an iPod favorites list forming. 
How about Garden Party? Remember that one? I don’t know that it’s particularly sappy, but it certainly reeks as a song.
Lest we forget, Clint Holmes sang the following in “Playground In My Mind”:
*See the little children
See how they’re playing so happy
In the playground in my mind.
Ba ba ba ba ba ba ba
La la la la la la la.*
To spare you all further brain damage, I have omitted the part where the rotten child sings “My name is Michael, I’ve got a nickel”. Hey kid, here’s a quarter if you’ll STFU.
Ladies and Gentleman I give you: I Hate Myself and Want to Die: The 52 Most Depressing Songs You’ve Ever Heard
Heh, sappy, not depressing.
“I Hate Myself and Want to Die” was a Nirvana song. It never seemed especially depressing to me, but it was of course prescient.
::shrug:: many of the songs listed here are in the book.
Nope. Got you beat. Don’t Take the Girl
Was the sappiest song I’d ever heard before “Butterfly Kisses.” Then they played it at my friends funeral. Now I want to puke and cry every time I hear it.
Does she die at the end or not? I never figured that out.
Since “Butterfly kisses” and “Christmas Shoes” have already been mentioned I’ll offer up:
Crystal Shawanda - You Can Let Go Daddy
It reads like a checklist of requirements for the most lachrymose song award.
From Sherman’s cite -
Perhaps that’s why Mommy and Daddy got into a big fight and Daddy left.
Who does Becky look like, the milkman?
Too bad! “Don’t Go Breakin’ My Heart.” You know how we roll around here!
Since all of the really sappy ones are taken, I nominate Foreigner: I Want To Know What Love Is.
I came in based on the thread title to say “Seasons in the Sun”, which is by far the sappiest song ever sung. I don’t see it disqualified by being worn out so much as that as you are looking for second place. Which would be “Patches”, a distant second, but still far ahead of anything which could be third place. Other songs are just cloying in comparison to these two. But you already knew these things.
Don’t give up on us, baby
We’re still worth one more try
I know we put our last one by
Just for a rainy evening
When maybe stars are few
Don’t give up on us, I know we can still come throooooooouuuuuuuuuuugh!
David Soul, for all of you blessed enough not to have this one act as an earworm.
[del]Ebony and Ivory, Silly Love Songs and My Love are all cloyingly awful.[/del]
Nope, the award should go to Yummy Yummy Yummy, by the Ohio Something-or-Other. Not only the sappiest, but possibly the worst song ever written.
These are epic schmaltz-fests, but let me throw up “She Can’t Help Herself” by Level 42. LSS, the subject of the song’s parents are killed in a car wreck, she’s sexually assaulted by a family friend, and she’s unable to find love. Mark King, the band’s vocalist, stated that he thought, “Bloody hell, what else can happen to this poor girl?” It’s a great song musically and vocally, but the lyrics are so horrible it makes me cringe.
Surely “Macarthur Park” has been mentioned in this thread? I just scanned it real quickly and didn’t see it.
In all seriousness, I retract my first nomination and replace it with the thread-winner: Dear Mr. Jesus.
This shows up in Texas on country stations around Christmastime. Does it make me evil for laughing at it?
Longer - Dan Fogelberg.
Longer than there’s been fishes in the ocean… this song has been sending me into a diabetic coma.
Please Daddy (Don’t Get Drunk This Christmas) - John Denver
Click the link… I dare ya!
Bastard! <glares in Hazle’s general direction>
I’d say most stuff by Barry Manilow, or as I like to call him: Barely Manenough. And Paul McCartney and Wings were none too sincere, either. How about “Ebony and Ivory”? That’s putrid. I know that’s Sir Paul and Jacko, but what the hell–Paul always was the Beatle with the worst case of treacle/smarm.
I hear the cottonwoods whisp’ring above
Tammy, Tammy, Tammy’s in love