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.

Janet Jackson "Together Again"

After graduating from college in 1999, I returned to my part-time DJ job at Windy 100 (WNND-FM) in Chicago. At that time, the upstart Adult Contemporary radio station was about a year old and had already eaten away at 93.9 Lite-FM's (WLIT-FM) stronghold on the market. The heritage radio station continued to present itself as an at-work radio station that shuffled through a "safe" playlist of ballads and without talk (DJs with personality). By contrast, Windy 100 pounded their mantra of "No Lite, Sleepy, Snoring, or Boring" music. While the station certainly did play some soft music (see "My Heart Will Go On"), it surrounded those songs with more upbeat tunes. Lite-FM eventually followed Windy 100's lead and added more contemporary and uptempo songs like "Together Again" from Janet Jackson -- music that the old Lite-FM would never play. By 2000, Windy 100 overtook The Lite in key demographics which led to a revolving door of personnel changes at 93.9 including their longtime Program Director and numerous on-air voices.

'N-Sync "This I Promise You"

My first foray into AOL chat rooms happened in 2000 when I sat using my mom's house computer one late Saturday night. While checking email, a pop-up box exploded onto the extra-large monitor that said "You live in Schererville???". Against any advice I would offer someone today, I responded with a resounding "Yes!" followed by a couple questions about how she knew this information and also who the heck she was. Some young girl who claimed to live in Schererville was on the other end of this message. At this point, I was actually living in Chicago, but my AOL account still listed me as living in Schererville, Indiana. After some more introductions, she asked what I did for a living. Instead of telling her about my full-time job (selling classified ads to dog breeders for a national magazine), I revealed my part-time gig: radio DJ at Windy 100 in Chicago.

Her response: "Cool. Do you play 'N-SYNC????"

"Indeed, I do," I said knowing that the only song we played was "This I Promise You" (which was written by former Adult Contemporary darling Richard Marx). She was pretty excited to hear this and promised to listen (I worked midnight until 5am, so I doubt she ever did).

From what I remember, I again heard from that same girl months later when I was back at my mom's house using her AOL. The second time her message was nothing more than "HEY!" so I certainly hope she finally found something else to do.

Sade "Smooth Operator"

Most people immediately name Delilah when they think about late night radio request shows and hosts, but those in Columbus and Chicago also will name John Symons and his "Love Notes" show. With his smooth baritone voice, Symons earned legions of fans in both markets for his years of playing love songs mixed with listener requests and dedications on the radio. Symons most recently worked for WLIT-FM in Chicago (coincidentally he replaced Delilah), but spent many years at cross-town rival Windy 100 (WNND-FM).

Peaches & Herb "Reunited"

How did I know the soft rock radio station where I was working in 2002 jumped the shark? After years of branding themselves as "never lite, sleepy, snoring, or boring", the station took a left turn and added burnt-out soft rock songs to their music library. This allowed "gems" such as "Reunited" to see the light of day. The result: it didn't feel so good. Ratings at the station dipped and within a few months the Program Director was fired followed by a complete format flip to an "all-80's and 90's" format.

The Alan Parsons Project "Don't Answer Me"

While working the weekend overnight shift during the winter of 2000, a woman named Jeanne used to call every night right around 2:30am (coincidentally the time when bars called last call). All of Jeanne's phone calls started innocently enough: she would request a song from Rod Stewart and tell me "he's sexy". Jeanne's voice when she said the word "sexy" was my first clue that something wasn't right with her. From there, Jeanne's conversation turned sexual. She would describe her underwear, the mirror on her ceiling, and even how wonderful her "female parts" looked. From the sound of Jeanne's voice, I would guess she survived on a steady diet of whiskey, scrap metal and broken glass. Being that I worked another job Monday through Friday on top of working at the radio station each weekend, I was usually running on caffeine and fumes at this point. A conversation with Jeanne was frightening for a 22 year-old bumpkin from Indiana (me), but also a source of entertainment since the radio station didn't have internet access or a TV...all we had was soft rock and lots of it. The request line provided my overnight shift with five streams of entertainment from over-served folks who dialed up the radio station. Throughout our many conversations, Jeanne gave me her Discover Card number to buy cologne (she called it her "Discovery Card"), invited me to sing karaoke, introduced her sister Millie (who lived downstairs) to the conversation, and also invited me over for Thanksgiving that year (I didn't go -- but later found out she also invited another jock as well. That tramp!) . I often wonder what happened to Jeanne and certainly hope that she finally got someone to enjoy that mirror on her ceiling...

Sophie B. Hawkins "Walking in My Blue Jeans"

I found an old aircheck from my days at "Today's Soft Rock" Windy 100 in Chicago.  Since it was recorded on a cassette tape, I managed to find a (working) cassette player to play said tape.  While I don't remember the song "Walking in My Blue Jeans", the Sophie B. Hawkins tune aired during an overnight shift on Windy 100 during the Spring of 2001.  The song peaked at #23 on the AC Chart in 2001.

Hanson - "MmmBop"

Radio stations became hot commodities after the Telecommunications Act of 1996 passed.  No longer were there strict ownership restrictions (companies could only own 20 radio stations and/or 2 per market).  National ownership caps were removed allowing companies to buy up as many stations as they could afford.  Suddenly, radio stations changed owners faster than you can say "deregulation".  Mom and pop stations started to cash out and sell to big radio companies.  The station where I worked was sold three times over the course of a year (making for a fun tax season!).  At one such meeting with the new owners, the General Manager announced the sale of the station to a room filled with dozens of people nervous about losing their jobs.  Without making any promises or revealing many details about the future of the station, the General Manager proclaimed the mantra to be "business as usual".  At the end of his speech, the afternoon jock raised his hand and said, "Chuck, I got a question."  Chuck said, "Sure.  What's your question?"  The afternoon jock cleared his throat and said, "Are we still gonna play Hanson?"  (long pause)  "Yes, we're still gonna play Hanson," the General Manager replied.  "Oh, good," the jock replied.  A few weeks later, the afternoon jock was fired.