The 20 Best Rap Songs

I remember when I was about to start at the American Enterprise Institute, and was being taken to different offices to sit down with and get to know various directors and scholars. Chatting with one fellow, I mentioned that I was born in Inglewood, Calif. “Ah,” he said, a smile creeping across his face. “Always up to no good!” Color me impressed: a conservative think-tanker had just quoted 2Pac. Days later, he quoted The Game.

It just underscored that ideology and even background don’t figure into the tastes of true music fans, something you’d never know by the assumption that those at a Republican rally just want to hear country (Alice Cooper, by the way, is a conservative — I expect to hear Welcome to My Nightmare at the next CPAC). I also had the added benefit of musical education from working at Tower Records (R.I.P.) in college. Many might remember the vast classical music rooms there, appropriately staffed by geniuses in the genre. While working undercover to catch shoplifters (yes, a cool job), I got schooled in everything from ska to opera. But my musical appreciation — capped by an undying love for records over CDs — has always been wide-ranging, from Frank Sinatra to Bob Dylan. And I’ve always loved rap.

So here are my top 20:

1. California Love2Pac with Dr. Dre and Roger Troutman
Probably 2Pac’s most crossover hit, this soars with the best of the state – “Let me serenade the streets of L.A.” With, yes, odes to Oakland and Sactown, the Bay Area and back down, as well. Best to hear while out for a cruise in the Golden State, even if it’s a tad cliche.

2. Ms. Jackson OutKast
I just love OutKast. This multi-Grammy-winning Atlanta duo — the first hip-hop CD to win Album of the Year (2004) — not only stormed onto the scene with their unique flavor of southern-fried funk, but has successfully put the music above the West Coast-East Coast rap feud drama that inundates the genre. The song is about a father getting shut out of his kid’s life by the maternal grandmother despite the fact that he meets his obligations and wants to be there. The video’s quite cool, too. (Explicit video)

3. Straight Outta Compton – N.W.A.
This hardcore original gangsta rap is my go-to MP3 selection to drown out noisy kids on the Metro. It’s also a historical piece of sorts by now, considering Compton is now just 33 percent African-American and 65 percent Hispanic due to black flight to the suburbs. N.W.A. was an early all-star rap group that included Dr. Dre, Eazy-E (who died of AIDS in 1995), and Ice Cube (who now makes family films and TV, showing that even gangstas grow up). (Explicit video)

4. Mama Said Knock You Out — LL Cool J
We’ve heard too many boxers use this as their opening motivational march into the ring, but it’s actually a song about climbing up the career ladder. LL’s grandmother gave him a bit of advice when his career seemed to be stuck in a rut: “knock out” the critics and believe in your talent. Hence he defiantly opens the song:  “Don’t call it a comeback/I’ve been here for years.”

5. Lose Yourself – Eminem
Another in the vein of motivational rap songs, I’ve listened to this on the way to an important interview more than once. It also helped salvage the reputation of white rappers after the damage done by Vanilla Ice. Chrysler also used the song by the Detroiter to try to salvage its cool factor after the auto bailout.

6. Gin and Juice – Snoop Dogg
Nowadays, Snoop Dogg gives Ron Paul two puffs up and tweets awesomely random things (my favorite: “Only white people eat Arby’s”). Back in the day, Snoop Doggy Dogg (from his parents’ nickname for him, “Snoopy”) was a young rapper from the LBC debuting on the Death Row Records label with this single, his second, that quickly climbed the charts. It’s got that summertime, gangsta version of “Home Alone” feel. (Explicit video)

7. Regulate – Warren G and Nate Dogg
Another from the Long Beach crew — and yes, there was a “Warren G Week” declared by the mayor in 2005 — but a decidedly smooth track. Totally fits for rolling with the top down — and it was amazing how often it came on the radio when I lived in Long Beach. Nate Dogg sadly passed away at age 41 last year after having suffered numerous strokes. (Explicit video)

8. Hypnotize – Notorious B.I.G.
This song not only was No. 1 on the charts after Christopher Wallace was gunned down in a drive-by shooting — a crime still unsolved — but was also his first song to break the top 10 in the U.K., showing the wide appeal for the man whom many consider to be one of the greatest rappers of all time. It builds off a 1979 Herb Alpert instrumental and Biggie’s easily flowing style. (Explicit video)

9. Around the Way Girl – LL Cool J
I have fond childhood memories of this song. My best friend and I got matching overall shorts (yes, the bane of 1990s fashion) and had to stand at a bus stop with lollipops, like the lyrics. We loved LL, yessir. This song perfectly highlights his silky rap-ballad style in contrast to the harsher delivery of “Mama Said Knock You Out.”

10. The Crossroads – Bone Thugs-N-Harmony
Yes, this song puts the harmony in rap. It’s actually a tribute to the late Eazy-E, released a year after his death. One of the few rap songs that has a beautiful musical quality about it.

11. Nuthin’ But a ‘G’ Thang – Dr. Dre and Snoop Dogg
One of The Rock and Roll Hall of Fame’s 500 Songs that Shaped Rock and Roll, this is a more sinister track that promises with “Compton and Long Beach together; now you know you in trouble.” Catchy and just an excellent pairing. (Explicit video)

12. To Live and Die in L.A. – 2Pac
Just put the top down and cruise under the ghetto bird (police helicopter). Probably marks the only time former Gov. Pete Wilson made it into a rap song, and the video features landmarks such as Johnnie’s Pastrami on Sepulveda. My only beef is the not-nice slur against onetime “California Love” collaborator Dre at the end, though that’s wasn’t unique for Tupac “Let’s Stoke a Rivalry” Shakur (i.e. he slammed LL Cool J because he thought he was too mainstream). (Explicit video)

13. Now That We Found Love – Heavy D & the Boyz
Heavy D passed away at age 44 from a pulmonary embolism, a clot thought to have formed during a plane ride, last November. The Jamaica native not only released this irresistible dance hit in 1991, rap infused with the era’s New Jack Swing, but was a businessman who would become the first rapper to head a major record label. The “overweight lover M.C.,” as he called himself, even hired Puff Daddy as an intern.

14. Tennessee – Arrested Development
This group sprang onto the scene in the midst of the gangsta rap heyday, trying to offer a rap alternative that was more spiritual and uplifting. This song frankly talks about challenges faced by the black community and the need to visit faith and the wisdom of one’s forefathers. “Now I see the importance of history/Why my people be in the mess that they be/Many journeys to freedom made in vain/Brothers on the corner playing ghetto games.” It’s also just a great song with a beat that’ll hook you.

15. Stronger – Kanye West
Yeah, Kanye is a whiny brat who should get the hook at most awards shows, and can’t exactly pretend to be gangsta from his middle-class suburban background (he actually started in the music biz as a respected producer). But the guy who was called a “jackass” by President Obama for bogarting Taylor Swift’s VMA acceptance speech in 2009 has, I admit, created some good stuff. This song from his third album, “Graduation,” samples Daft Punk and Nietzsche and is another one of those motivational rap songs.

16. Signs – Snoop Dogg
One of the tracks off Snoop’s excellent 2005 “Rhythm & Gangsta,” it showcases the rapper’s more mature style. This extremely danceable track includes Charlie Wilson of The Gap Band and Justin Timberlake. I literally cannot sit still when this song is on. (Explicit video)

17. Big Poppa – Notorious B.I.G.
Biggie deserves another spot on this list. To be sure, there are various hits of his that could compete for this spot, but this smooth jam is the winner. (Explicit video)

18. Let Me Ride – Dr. Dre
The video is a winner simply for the sheer number of cars bouncing on hydraulics. From the classic triple-platinum Dre album “The Chronic,” this ode to low riders doesn’t make any broad social statements or pleas for social justice. It’s just about riding slow and low through the streets of L.A. (Explicit video)

19. Gangsta Nation – Westside Connection
From the 2003 album “Terrorist Threats,” this included rappers Ice Cube, WC and Mack 10 (another Inglewood native) and featured Nate Dogg. Love the beat and the video has an excellent mocking of the pants-on-the-ground trend. (Explicit video)

20. Bring Tha Noize – Public Enemy and Anthrax
Walk This Way (Run DMC and Aerosmith) is a great song and crossover collaboration, but I thought this was a truly original and effective pairing of two hardcore artists from their respective genres. It reminds us that Flavor Flav was always a joke and Chuck D was the real meat of Public Enemy, and was originally cut as a single that gave a nod to Anthrax. The groups then covered the song together. Fight-the-establishment rap and metal, as Chuck D would say, “made too much sense.”

Honorable Rap-Tribute Mention

Boyz in the Hood – Dynamite Hack

An acoustic version of one of N.W.A.’s hits, it’s downright hilarious. (Explicit video)