Whitney Houston "I Learned From the Best"

After stumbling upon a former colleague's website, I read this message: "Rob is retiring from radio." After years of traveling the country and holding down various radio jobs in Chicago as well as Las Vegas, he was hanging up his headphones and transitioning into web design. It was 1999 and everyone wanted a website, so Rob made the career decision to exit radio. His message included a zillion people he wished to thank including "Todd and Todd". Hoping I was one of the Todd's, I quickly found the "Contact Us" page and fired off an email. "I'm one of the Todds, I hope!"A couple days later, he confirmed that I was one of those he mentioned as being a "joy to work alongside" -- I was flattered. 

Sting "My Funny Friend and Me"

Disney's The Emperor's New Groove didn't exactly light up the box office, but it did make them plenty of cash. Its soundtrack also produced the Sting ballad "My Funny Friend and Me". Much like the movie itself, the song wasn't a huge hit (reaching #24 on the Adult Contemporary Chart).

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.

Everclear "Wonderful"

Aside from being some shitty liquor you happily drank as a teenager, Everclear is also a rock band from Portland that provided us with such late-'90s angst as "I Will Buy You A New Life", "Father of Mine" and "Wonderful". Despite the catchy tune's optimistic title, the song is told from the point-of-view of a child who sees their parents constantly argue and bicker.

Phil Collins "Strangers Like Me"

"Are you okay?" I heard as I sat staring out the window of the Kinball-bound CTA Brown Line train.
"Um, are you okay?" I heard again.
I looked up and saw two strangers staring at me from across the aisle.
"Who, me?" I gingerly replied.
"Yeah. You look so down. Are you okay?" she asked again.
"Oh. Yeah. No, I'm fine. Just lost in thought I guess."
"Oh, okay," she said and went back to her conversation with her friend.
This happened three days after 9/11 and the genuine concern that stranger showed remains with me today.

Oscar de la Hoya "Run to Me"

Oscar de la Hoya, the former boxer and potential 2020 presidential candidate, once charted a song on the Adult Contemporary Chart. The "Golden Boy of Boxing" remade the Bee Gee's tune in 2000 and managed to turn the ballad into a minor radio hit (peaking at #23).

Barenaked Ladies "Pinch Me"

In another case of "Oh, no...I guess I'm not young anymore", '90s radio staples Hootie & the Blowfish will team up with Barenaked Ladies for a 2019 tour. Their forthcoming "Group Therapy Tour" will celebrate the 25th anniversary (hot damn, 25 years ?!?) of Hootie's super-duper mega-successful Cracked Rear View. Yes, the album that featured five singles Adult Contemporary radio stations played to death. As a young radio intern during the fall of '95, listeners would send faxes to the radio station begging to stop playing Hootie songs. In fact, I think it's a brilliant promotional idea where you promise listeners you won't play a certain artist's music for an entire day/weekend -- think: "No Adele Weekend" or "Taylor Swiftless Tuesday". It could happen...

Backstreet Boys "The One"

Usually a record company decides which singles from a band's album gets released to radio stations. In the case of the Backstreet Boys, they left that decision up to let the fans to choose courtesy of MTV's TRL. Four of the band's members voted for the song "Don't Want You Back", but Nick Carter had other plans. He called into TRL and voted for "The One". His legions of fans followed and up-voted "The One" -- making it the group's final single from their Millennium album.

Whitney Houston & Enrique Iglesias "Could I Have This Kiss Forever?"

"Could I Have This Kiss Forever?" won an award from the publication Idolator for being the #1 song from Whitney Houston that radio forgot. While that award title might elicit a head scratch, the sultry ballad featured Enrique Iglesias and appeared on radio stations in late-2000 before apparently falling off the map. If you're curious, other songs that made the list include "Million Dollar Bill" and "My Love Is Your Love".

'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.

Vertical Horizon "Everything You Want"

What did you buy your significant other for National One-Hit-Wonder Day? Nothing, huh? Well, another One-Hit-Wonder Day came and went in September and I missed it. Given how Mattress Firm didn't hold a "One Hit Wonder Mattress Sale", this blessed day clearly is of no concern to most except for radio DJ's and folks at Newsweek who are hard-up for a story that doesn't involve politics. Alas, they published a list of the best-charting one-hit-wonders from 1980 until 2012 and boiled it down to these Top 5 One-Hit-Wonders:

1. Gotye "Somebody I Used to Know"
2. Carly Rae Jepsen "Call Me Maybe"
3. Los del Rio "Macarena"
4. Vertical Horizon "Everything You Want"
5. James Blunt "You're Beautiful"

In the case of Vertical Horizon, their 2000 hit "Everything You Want" wasn't their only hit as "You're A God" followed and climbed to #23 on the Hot 100 so this list is bunk...

Samantha Sang "Emotion"

Her first name might not be Samantha (it's Cheryl), but her last name is definitely Sang. After beginning her career as Cheryl Gray, the Australian changed her name to Samantha Sang signing on with Barry Gibb's manager. Gibb was such a fan of hers that he even sang backup vocals on "Emotion". The tune is Sang's biggest hit to-date. Destiny's Child covered the song in 2001--leading some Adult Contemporary radio stations to spin the tune again.

U2 "Beautiful Day"

U2 struck gold in 2000 with "Beautiful Day" and, 10 years later, another artist would turn the song into a Top 40 hit. American Idol contestant Lee DeWyze won the ninth season of the reality show and chose to cover the song. It remains his biggest (and only) Hot 100 hit for the Mt. Prospect, Illinois native.

Tamara Walker "Didn't We Love"

Things we loved in the year 2000: young girls in skimpy clothing dancing on bars. In this case, it wasn't bar patrons, but rather bar staff donning leather pants and cowboy boots while dancing on the bar top of country bars all across America. Credit the movie, Coyote Ugly, for jump-starting the trend.

Incubus "Drive"

Chicago's volatile airwaves changed yet again on April 2, 2001 when, after weeks of stunting, 97.1FM became The Drive. Armed with a quarter of a million dollars in research, The Drive set out a new journey for Classic Rock in Chicago -- the station featured no contests, no morning show and no hype...just rock 'n roll. The station's playlist dug deeper than your standard "Hotel California" and "Layla"classic rock songs to bring back those deep cuts that disappeared from radio at the time. The voice of The Drive belonged to Nick Michaels--the ultimate storyteller who made the music and the listener the star. Given its no-hype persona, no voice but Michaels would do. His no-nonsense delivery when saying "this is the soundtrack of our lives" still resonates today. Sadly, Michaels passed away of a heart attack on May 26, 2018.

Faith Hill "Breathe"

Not once did Faith Hill's "Breathe" notch the top spot on the Hot 100 in 2000. Despite that, Billboard crowned the ballad "Song of the Year"--making it just the second time in history a song never hit #1, yet won "Song of the Year". It happened again a year later when Lifehouse's "Hanging By A Moment" shared the feat.

Don Henley "Taking You Home"

Being a part-time radio DJ meant that you held down another full-time job (usually outside of radio) and you generally only worked weekends and holidays. However, the reality is that your boss could phone you and ask you to cover a shift with little to no notice.

One night, late in the evening, my roommate knocked on my door to tell me that my boss was on the phone. I immediately knew he would be asking me to cover the overnight shift. That next day, my corporate boss from the New York publishing company where I worked was holding an important morning meeting that I needed to attend. He rarely traveled to our office and also had a name much like an adult movie star, so I was eager to meet him. I explained this to my boss who assured me that I would only have to cover from midnight until 1:30 A.M. because Kelli, another part-time DJ, would take over from there. Kelli worked as a bartender at a restaurant that closed at 1:00 A.M. and she would drive to the station immediately afterward. I was a sprite young 24 year-old who could easily bounce back from a night with five or six hours, so I agreed to work with the understanding that I would be home by 2:00 A.M.. My boss thanked me, and I hopped in a cab and headed to work.

Around 1:45 A.M., the radio station's hotline rang. The hotline is a special phone number that only employees of the station knew and used. It's rarely a good thing when the hotline rings (in fact, most stations have a strobe light that flashes to alert you when someone is phoning the hotline). Usually, that line is reserved for an angry Program Director calling to tell you what you did wrong or for fellow DJs to tell you they're running late. Kelli, who was already 15 minutes late, called to tell me she was in a car accident and would be late. Kelli's voice sounded shaken and frail. She said she wasn't injured and had to wait for the police to file an accident report and possibly might need a tow truck for her SUV. Remembering my early morning meeting at my other job, I asked her not to worry, just do what she needed to do and keep me posted. Nearly an hour later, she phoned again to say that she was almost done with the police and would soon be on her way...provided her car would cooperate. At this point, it was nearly 2:00 A.M. I told her not to worry about coming into work--I would cover the entire shift. Relieved, Kelli thanked me and told me she would pay me back somehow. I hurriedly phoned my boss's office at the magazine and left a voicemail explaining what happened and to say that I would be a little late coming into work in the morning.

With a solid two to three hours of sleep, I dragged myself into work later that morning but could not find anyone at their desks, in their cubicles or even in the company's break room. My boss' office door was closed, so I knew at least someone was there. Plus, there were purses and briefcases strewn about other people's cubicles, but no other people. I dropped my coat and backpack down and sat at my desk to check email and voicemail. Aside from the usual client email, I noticed an email from our corporate market manager with the porn star name. Before I could read the contents of the email, my boss was standing behind me and asked me to join him in his office. I walked with him to his office where he introduced me to a man sitting at his desk--at last, I finally met the corporate boss with the porn star name! This portly man (who was definitely not a porn star) informed me that our parent company discontinued one of the magazines in our office and also dismissed all but five people from my office. The Chicago office housed production, sales and editorial whereas our New York office contained billing, circulation and the corporate big wigs. Gone were our editorial and production folks including people I hired as well as others with 30-some years of service. Somehow, I was one of the five whose jobs were spared. When my boss at the radio station called me that afternoon to thank me for covering the entire overnight shift, I filled him in on the mass firings. He apologized again and promised to repay me in some way. Before too long, he would help rescue me from my job at the failing magazine with a newly created job at the radio station....

Evan & Jaron "Crazy for This Girl"

The secret to getting your song on the radio in 2000? First, make sure your song aired on an episode of The WB's Dawson Creek. Then, make sure two handsome twin brothers (such as Evan & Jaron) perform the song. The duo turned their simple ballad "Crazy for This Girl" into a hit thanks to some help from Dawson, Pacey and Joey. (Editor's note: The cast of Dawson's Creek reunited this week for an Entertainment Weekly issue celebrating the show's 20th anniversary and the cast pondered the thought of a reboot a la Roseanne.)

Matchbox 20 "If You're Gone"

Rob Thomas carried so little faith in the song, "If You're Gone", that he didn't even expect it to make the band's Mad Season album. Instead, the song exceeded his expectations and went to #1 on the Adult Contemporary Chart and even climbed to #5 on the Hot 100 in 2000. If that wasn't enough, the brassy ballad finished fifth on the Year End Chart in 2001.

Aerosmith "Jaded"

Aerosmith performed their new single "Jaded" during a star-studded Superbowl halftime show in 2001. *N-Sync, Mary J. Blige and even Britney Spears also appeared. "Jaded" remains Aerosmith's last Top 10 hit on the Hot 100 Chart.