Here's a list of a few ultimate guilty pleasures of mine...the list could go on and on but here are some notables....
Rick Astley - "Never Gonna Give You Up" (1987)
#1 Billboard Hot 100 hit
This song is just so addicting, I can't help but listen to it...over and over again. Apparently, 12 1/2 million people who have viewed the video on YouTube agree with me.
Of particular note is the mashup of this song's vocals with the music of Mika's "Happy Ending"...gives the song and particularly its lyrics a haunting, visceral quality. (Listen to that version here: http://www.youtube.com/watch?v=uDI-PCDL2G4)
REM - "Everybody Hurts" (1992)
#29 Billboard Hot 100
"When the day is long...and the night, the night is yours alone....." Man, this song just makes me want to cry sometimes...unless you just embrace it. I once used this song in a documentary in a post-modern ironic sort of way...and by ironic I mean it was half-serious. As I always say, never underestimate the power of Oprah. And this song. Because sometimes, everything is wrong.
Backstreet Boys - self titled (1997)
#4 Billboard Top 200 Albums, 14x platinum (diamond)
What a classic! It reminds me of being in the 6th grade and absolutely loving everything the Backstreet Boys put out. Highlights of this album are: "Everybody (Backstreet's Back)" - a classic track that everyone can still do the dance to, "If You Want It To Be Good Girl (Get Yourself A Bad Boy)"....a sexual come on if I ever heard one, "Hey Mr. DJ (Keep Playing This Song)" and "All I Have To Give". There is no more rabid and loyal fanbase then teenage girls (witness the modern day success of the Jonas Brothers and Twilight) and in 1997, the BSB were the object of their desire...and would remain so for the next 5 years or so.
Kid Rock - "Only God Knows Why" (1999)
#19 Billboard Hot 100
OK this song is not quite as guilty of a guilty pleasure as the other songs I have compiled for this entry, but it was a song that I don't think people anticipated of Kid Rock at the time. He had already released "Batwitaba" and "Cowboy" off the album Devil Without A Cause (1998). Those two songs could not have been more different from "Only God Knows Why" - a country-tinged ballad about being on the road too long much in the vein of Jackson Browne.
I think this song attracted Kid Rock some fans that would follow him when he released "Picture" in 2002 and "All Summer Long" in 2008. Interestingly, according to Wikipedia, Devil Without a Cause is currently one of the three records with a parental advisory label to be certified Diamond, the other two being Outkast's Speakerboxxx/The Love Below and The Notorious B.I.G.'s Life After Death."
Will Smith - "Will2K" (1999)
#25 Billboard Hot 100
This ode to the new millennium - it's here and I like it - still holds up to this day even if several New Year's Eves have passed since its release. This song reminds of me of a particularly memorable New Year's Eve party in New Jersey circa 2006 where this song was played about 5 times that night. This may be the world's catchiest song. Just try to resist. Why this song made it to Blender's 50 Worst Songs Ever list is beyond me, because it is Just. Awesome. So. There.
Ashlee Simpson - "Autobiography" album (2004)
#1 Billboard Top 200 Albums hit, 3x platinum
OK, this is a little embarrassing but I can still listen to this album start to finish. Ashlee may not have the best voice in the world, but the songs are catchy and creative. It's unfortunate that after this promising debut as sort of the anti-Jessica Simpson, her nose job, sexier clothes, and dyed hair made her look exactly like her sister. The highlights of this album are "Surrender", "LaLa", "Pieces Of Me", "Shadow" and the sadder ballad "Unreachable".
T-Pain featuring Yung Joc - "Buy U A Drank (Shawty Snappin')" (2007)
#1 Billboard Hot 100 hit
Anyone that knows me knows my odd obsession with singing this song...over and over. Enough said.