30. “Only Hope” – Switchfoot (1999)

A ballad with so much hit potential that Mandy Moore wanted to sing it in her hit movie, A Walk to Remember. Before it was heard by millions on the big screen, it was released on an indie album called New Way to Be Human. Jon Foreman has had a fair amount of really good songs over the course of his career, but I think this is his finest moment.

29. “Southtown” – P.O.D. (1999)

I credit “Last Resort” by Papa Roach for getting me interested in nu-metal. Did I say credit? Maybe blame is a better word. Anyways, this first single from The Fundamental Elements of Southtown is what caused me to go all in with nu-metal for a few years. Many of the songs in that style make me cringe these days, but this one still rock’s the party all night long…even more so than the P.O.D. song that’s about doing that exact thing.

28. “Carried Away” – Sonicflood (1999)

This song, from Sonicflood’s self-titled debut, sounded SO epic to me and my limited music experience when I first heard it. I’m guessing it was because of the things I still love about it today; the orchestral sound combined with the loud guitars, the incredible guitar solo, and Jeff Deyo’s vocals.

27. “Don’t Speak” – No Doubt (1995)

This breakup anthem from Tragic Kingdom was all over the radio in the mid-to-late 90’s. I remember being bummed that they didn’t release a CD single of this song. An $18 full-length album wasn’t all that affordable for a 13 year old, but a $2 single? I could easily convince someone to buy that for me! That was how most of my early music collection was formed, by asking parents and grandparents for CD singles. So the frustration that No Doubt put me through, with this being the only song I can ever remember loving, yet being mad at, is why “Don’t Speak” is number 26 instead of…I dunno, 24 or 25.

26. “Like I Love You” – Amy Grant (1997)

I wouldn’t consider myself a very big Amy Grant fan, but Behind the Eyes has several excellent songs on it. One of those fine songs is this non-single where Amy is assuring someone that she’s never gonna leave (Side Note: I really hope this wasn’t written to comfort Gary Chapman). I forgot about this track for a few years in the 2000’s, but when I returned to it, I was reignited with the cozy, yet melancholy feeling I get when this one plays.

25. “Frail” – Jars of Clay (1997)

Surprisingly, this is the first song from my favorite album of the 90’s, Much Afraid, to make an appearance on this list. Have no fear (pun intended) , there’s more to come from that album. Jars are fantastic at slowing down and getting all chamber-sounding on us, as heard here. This song was first released in 1994 on the first (very hard to find) Jars of Clay album, Frail.

24. “Alcatraz” – Fono (1999)

I have probably forgotten most of the things I learned in 1999 that aren’t all that applicable in my daily life, but it’s going to be hard for me to forget that Leon “Whitey” Thompson was a man who was dead inside. This is the third song you’ve seen on this list from the largely unknown modern rock juggernaut Goesaroundcomesaround, but if you check out one song from that album, let it be this one. If the huge sounding drums and powerful riff that open the song (after a sample of Mr. Thompson telling us how he found himself in Alcatraz) doesn’t make you feel something, maybe you can also identify as being someone who is dead inside…or someone with different taste in music than I. Probably the former, though.

23. “Keep Waiting” – Stavesacre (1999)

1999 was a pretty monumental year for me. Nope, it was not the year I got my drivers license or graduated high school…it was the year I got the Internet. Thanks to good ol’ dial-up, I discovered exactly what I was looking for at the time, ChristianRock.Net. I was familiar with all of the big Christian rock bands, like DC Talk and Audio Adrenaline, but I knew nothing about Tooth & Nail Records and alternative Christian music. Through the website I was introduced to this amazing world that I didn’t know was out there. The first song I remember catching my attention on ChristianRock.net was this one, and I’ve loved it ever since. I eventually picked up the incredible album this song was released on, Speakeasy, which I also still very much enjoy to this day.

22. “All These Years” – Sawyer Brown (1992)

From Cafe on the Corner, this song does what a sad country song is supposed to do, makes me want to hide behind the tractor and cry my eyes out. Without going into detail, the subject matter here is something that I’m very sensitive about, so I’m sure that doesn’t help keep my eyes dry when I sink into this song. Besides all of that, this is just a well-written song with excellent vocals by Mark Miller.

21. “Live the Life” – Michael W. Smith (1998)

Michael W. Smith goes in a mildly psychedelic direction on the lead single from Live the Life, and it actually turned out great. There’s also some really good David Gilmour-esque guitar going on at the end. Aside from having the standard MWS power-chorus, this a pretty gutsy call for a lead single by a pop star near the height of his popularity.