Jon Secada "Stop"

As Rob Thomas and Santana's "Smooth" dominated the radio well into Y2K, Jon Secada followed suit with his spicy uptempo "Stop". With an abundance of "Latin Explosion" artists like Ricky Martin, Marc Anthony and Christina Aguilera's all over the radio at the time, "Stop" got lost in the shuffle and the song barely registered on the Adult Contemporary Chart.

Madonna "Holiday"

My friend's parents stocked up on canned peaches in fear of the year 2000. Y2K scared many folks into believing the world would end because our computer systems were ill-prepared to handle the transition from a year beginning with "19" to the year 2000. While working at soft rock Windy 100 in Chicago on New Year's Day 2000, I arrived nearly two hours early and nervously stared at the computer as the clock flipped from 1999 to 2000 with Madonna's "Holiday" playing. Somewhere in my basement, I still have the memo from my boss detailing what to do in case Armageddon happened.

Lou Bega "Mambo No. 5"

Some worried their banks would lose all their money, planes would fall from the sky, and computers would all cease operating once the calendar turned to 2000. Seemingly oblivious to it all, Lou Bega mamboed through it all with his friends Monica, Erica, Rita, Tina, Sandra, Mary, and Jessica.  Bega's remixed version of the 1949 hit from Damaso Perez Prado helped the world forget about Y2K and focus on more important things.

Backstreet Boys - "Show Me The Meaning of Being Lonely"

The last day of the year 1999 was riddled with Y2K fear.  Airplanes would fall out of the sky.  Our computers would all crash.  And the banks would surely all fall victim to the Y2K bug leaving us penniless (unless you withdrew a huge sum of cash and stashed it in your Y2K Shelter--also known as a "basement").  To restore order, the United States government deployed The Backstreet Boys.  Thankfully, their lush soothing voices in "Show Me The Meaning of Being Lonely" extinguished all the fears and the panic that weighed heavily on the shoulders of all Americans.  Suddenly, all was right with the world.

Christopher Cross - "Arthur's Theme (Best That You Can Do)"

Let's put an end to a fight that started well before Y2K: Newman's Newmannnium Party trumped Kramer's Millennium Party because Newman had already booked Christopher Cross (and the revolving restaurant that overlooks Times Square).

Ricky Martin - "She's All I Ever Had"

The year 1999 will be remembered for the craziness surrounding Y2K. Wait, you didn't stock up on canned peaches while storing all your money under your mattress? Some folks did. Aside from the Y2K lunacy, 1999 gave us the "Latin Explosion" with names like Santana, Jennifer Lopez, and Ricky Martin dominating the radio. While "Livin' La Vida Loca" has stood the test of time, Martin's follow-up hit "She's All I Ever Had" now sits next to that can of expired cling peaches from your parent's Y2K shelter.