Hmm, sorry in advance for what I'm going to do to you.
I will begin with a Top 10 but probably I'll get to post a Top 25 later. Not easy for me to find so many songs because I want to impose myself some restrictions of what a guilty pleasure means in my case. I can't feel guilty for liking a feel-good or happy song, so many Disco or Pop songs are not guilty pleasures in my book. I also don't feel guilty for liking some very popular, mainstream songs. So I'll mainly include songs overly melodramatic and sentimental shamelessly aimed to pull at the heartstrings of the audience, songs in which I can perfectly detect the tricks the writers and performers employ to extract from me goose-bumps (or even tears) but despite this I can help but not only like them but LOVE. And play "repeat" after the end. That's why I won't post a Top 100, it ought to be songs that move me (at least if I'm in the mood).
1. TED NEELEY "
Ghetsemane (I Just Want to Say)" (1973)
A song I discovered (and loved) when I was a child, before learning about tastes (and all the prejudices that come with learning). "Gethsemane" was the central piece of the musical "Jesus Christ Superstar" and it was written as a prayer from Jesus Christ to God expressing his doubts before his passion and crucifixion, with a strong emotional content ranging from fear to anger but ending with acceptance. The original version was part of a concept album released in 1970 and was sung by Ian Gillan of Deep Purple fame (this version still can be considered almost cool, you can listen to it
here). But the one I like the most was sung by Ted Neeley for the 1973 motion picture. I know that those spine-tingling (or ridiculous, depending on the side you're on) falsettos from 2'25" to 3'25" are Gillan's but the part from 3'57" was the part when Neeley wins it for me. While Gillan's sticks to the melody of the first part Neeley makes an impressive transition from the defeated whisper of "now I'm sad and tired" to the final piercing growl of acceptance in "I will drink your cup of poison, nail me to your cross and break me." It's strange because despite my catholic upbringing now I consider myself an agnostic. But what can I do? This song still send me chills every time I revisit it. Verdict? Guilty, of course.
2. ELECTRIC LIGHT ORCHESTRA "
Xanadu" (2000)
Not a case of an overblown song this time but surely cheesy. In fact this is a big pile of cheese. Electric Light Orchestra could well be the ultimate guilty-pleasure band to me but I should admit that I don't feel guilty at all for liking ELO's 70s output. "Strange Magic," "Livin' Thing," "Mr. Blue Sky" or "Last Train to London" are in my book great songs. Period. But their 1980s releases are a different thing, especially the soundtrack of "Xanadu." I remember at the time (15 years old) thinking they have gone too far, they've put too much cheese this time. But last summer I stumbled with the re-recording Jeff Lynne did on the late 1990s (the original as you all know was sung by Olivia Newton-John in 1980) and was mesmerized by the twists and turns of the melody and the splendid chord sequence (especially the Dm after the B on the chorus). Not the perfect pop song ever maybe but surely an addictive one.
3. CLAUDIO BAGLIONI "
Sabato pomeriggio" (1975)
The Italian ballads. In Italy the melodramatic ballads are secular traditions, from the Neapolitan traditional songs to the Operatic arias the singers had always addressed their loved ones as in a serenade, trying to win their hearts putting all their soul on their singing. I was reminded (also) last summer of this Baglioni song when I compiled the Spotify playlist for the 10,000 songs (even if ended bubbling under), a song that was at the back of my mind as a vague remembrance of my childhood. The song was part of a concept album depicting vignettes of a Saturday afternoon (English for "Sabato pomeriggio") in a big city and the tittle theme was the album closer. The song begins as a typical Italian piano ballad but then at 1'38" a mellotron enters (with probable influence of the contemporary 10cc's "I'm Not in Love") followed by the strings giving a dreamy ambiance while Claudio sings raising an octave "senza te morirei" ("without you I will die"). And I surrender. Guilty again.
4. STOCKARD CHANNING "
There Are Worse Things I Could Do" (1978)
"There Are Worse Things I Could Do" was part of the soundtrack of the movie "Grease" and was sung by Stockard Channing on her role of Rizzo. The song is a monumental piece of schlock, kitsch or whatever other German word you want to use but in my opinion it succeeded in depicting the vulnerability that lies at the core of the archetypical bad girl. Also recommended are the Jazz-Pop cover by
Alison Moyet or the spare cover by
Bonnie 'Prince' Billy.
5. CULTURE CLUB "
Victims" (1983)
Another overblown piano ballad, with all the elements they could put on the mix to make it grandiose, including orchestral flourishes with strings, horns, oboe and harp, a gospel choir and and a rhythm section making a grand entrance at 2'17" and doubling the tempo at 4'02" only to slow it down for a final fanfare. The video clip is even more excessive (with this bellboy carrying the harp for the last chord). What saves this for me? Of course, Mr. George O'Dowd and his soulful vocals.
6. KEANE "
Everybody's Changing" (2003)
Yes, I know. If Coldplay are a watered-down version of Radiohead, Keane are a watered-down version of Coldplay. But what can I do? When the piano plays that ascending line at 2'44" I have to surrender again. Note: the only song on my Top 10 included on the AM Top 10,000.
7. BECK "
Everybody's Got to Learn Sometime" (2004)
The real guilty pleasure would have surely been to chose
The Korgis' original (1980) but Beck's cover is quite cool in fact, isn't it? Especially when matched with images of the splendid Michel Gondry film "Eternal Sunshine of the Spotless Mind."
8. ELVIS COSTELLO "
She" (1999)
I remember myself thinking when the song was released that in any other voice (including even the 1974 original by
Charles Aznavour) would be extremely kitsch but since it was Elvis Costello who sang it the song should be extremely cool. Excuses for not feeling guilty. This time the song is matched with images of the not-so-splendid Roger Michell movie "Notting Hill."
9. DAMIEN RICE "
Amie" (2002)
Even Damien Rice should be aware of the seriousness and sentimentalism of the song because every time he plays it live makes a long and humorous
intro speech to play the matter down. In vain. Only the strings outro is surely more sentimental that anything on this list. And there's nothing wrong with that.
10. JOSÉ EL FRANCÉS con la colaboración especial de NIÑA PASTORI y VICENTE AMIGO "
Ya no quiero tu querer" (1999)
The Spanish quota. During the 1990s a style rose in Spain that was pejoratively called
Flamenquito because watered down the rawness of real Flamenco, fusing it with Italian balladry. But sometimes the results were brilliant in its cheesiness like this remake of "Ya no quiero tu querer," "I Don't Want Your Love" (the original from
1993 was simpler and rawer).
I just realized that almost half were covers or remakes. Well, I think I've embarrassed myself enough for today. But I'm afraid I will return in a few weeks/months feeling guilty again.
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Great start! I must confess: some of the songs already mentioned are ones I didn't know I should feel guilty about liking. I think I'll base my list on songs that are already mentioned in lists, as well as those I know I should feel guilty about (so much so that they don't even make anyone else's list).
I than discovered all genres whether “smart, intellectual and sophisticated” or “pop oriented and hooky” have highs, lows, under appreciated and overrated acts. Certain genres however get more prestige than others though. Some acts deserve it some acts don’t. 
