Rap Music: When Comedy Meets Poignancy

There are a couple things you may not know. First, this is Hip Hop Appreciation Week. Yes, it’s an actual thing. And second, hip hop is my second favorite genre of music. It may be hard to believe, but it’s true. Second only to my love of instrumental motion picture scores is my love of rap.

In fact, I’ve played around with the possibility of writing and recording some of my own rap music. If I did, you could then call me by my hip hop name: Skittles. (M&M is already taken…sort of.)

Rap songs have the unique ability to contain boatloads of information, which, depending on how the format is utilized, can lend itself well to either serious and weighty meditation or outlandish humor. I love both uses. So, in honor of Hip Hop Appreciation Week, I wanted to share some of my favorite rap songs/videos with you. I don’t necessarily think these are the cream of the crop from an aesthetic standpoint—only that I myself enjoy them immensely. I’ve divided my list into two groups: humorous rap songs and serious rap songs. We’ll start with the humorous ones first.

Top 5 Humorous Rap Songs

5. “Yo Mama Battle (of Compliments)” (Rhett & Link)

It’s hard to pick a favorite of Rhett and Link’s hip hop songs, but I like this one because of the twist on a rap battle (i.e., compliments instead of insults) and the cleverness of the lyrics. (My wife likes the “Epic Rap Battle of Manliness” better.)

4. “White and Nerdy” (Weird Al)

Weird Al’s parody skills are exceptional, and this hip hop song is…well, no exception.

3. “Tears of a Rapper” (Flight of the Conchords)

This song comes from the Fight of the Conchords TV show. The lyrics this dynamic duo comes up with are often hilarious. Unfortunately, the song cannot be imbedded, so here is the link. (Warning: song contains some language.)

2. “See You on Monday” (Roman Johnson)

Slathered with delicious lyrics, this song about a man pining for Chick-fil-A on a Sunday (when the restaurant chain is closed) is a real treat.

1. “Swagger Wagon” (Toyota)

Created by Toyota (yep, the car company), this is a clever and slick piece of marketing. As a standalone song (and music video), it’s an intense and entertaining laugh-fest.

Top 5 Serious Rap Songs

5. “Can I Live?” (Nick Cannon)

This song wears its message on its sleeve, but I still love it for two reasons: 1) it’s a message I’m passionate about, and 2) the “twist” ending gives the piece a nice rhetorical boost.

4. “Atonement Q&A” (Shai Linne)

This is a theologian’s dream: a hip hop catechism. Through a series of questions and answers, Shai Linne explains the nature, extent, and beauty of Christ’s atonement.

3. “The Interview” (Timothy Brindle)

Although this could technically fit in the humorous category, it still deals with a serious topic: finding and rooting out the sin in one’s life. Arranged in the form of an interview, and filled with clever lyrics/banter, this song expertly sets up the rest of Brindle’s Killing Sin album. (Yes, I know the album’s artwork leaves much to be desired; just focus on the words of the song.)

2. “Far Away” (Lecrae)

Written as a source of encouragement to those experiencing suffering, Lecrae dedicated all royalties to this song toward relief work in Haiti after a 2010 earthquake killed hundreds of thousands of people.

1. “Rebel” (Lecrae)

Lecrae is my favorite rapper, so it’s hard to pick my top selection from him. At long last, I decided on this one simply because I listen to it more than just about any of his other songs. (This music video is not officially from Lecrae, but I found it more visually interesting than those with just words on the screen.)