DISCLAIMER: This post will be mainly '90s hiphop, with a few exceptions
Skee-Lo - I Wish
This song is just so much fun to jam out to. Skee-Lo definitely isn't my favourite rapper, and honestly I'm not even that big a fan of his other songs, but this song just gets me every time. Everything about it is catchy, it's upbeat, and at least for me it never gets old.
Souls Of Mischief - 93 'til Infinity
This song honestly has one of the best beats I've ever heard in a hip hop track. Doesn't matter what's going on, where I am or what I'm doing, I can always put my earphones in and just completely chill out to this song. Unfortunately I didn't know about this song up until like a couple years ago, so I'll only be chillin from around 09 'til infinity :(
Shad - I Get Down
This is probably ganna be the only recent song (as in 2005) on my list here. Shad's kinda different from most hiphop artists in that he never swears and focuses a lot more on wordplay and flow. Because of this, rather than jam out to his stuff I usually just put the ol' earphones in, close my eyes, and just get absorbed into the words he spits out. I really suggest to anyone who's gonna listen to this to do the same; I always seem to find new metaphors and puns every time I listen to one of his songs and it always makes me smile.
Nas - Represent
Nas is probably (or at least, should be) a familiar name to anyone remotely familiar with hiphop, and for good reason. This song is probably what first really got me into Nas, and so it's the first song that comes to mind when I think Nas. His flow in this song is just unbelievable, the beat is awesome, and overall I just love the song. The second verse in particular is my favourite
The Pharcyde - Ya Mama
YA MAMA GOT AN AFRO WITH A CHINSTRAP
This song is just exactly what I love about The Pharcyde, and specifically the album this song is from (Bizarre Ride II the Pharcyde): the dudes are just having fun. There's no deep messages or anything, just 4 guys rapping and making ya mama jokes back and forth. The song is just always fun to both listen and jam out to.
Gang Starr - Moment of Truth
This is another song that I love to listen to with earphones on, eyes closed, just listening. The beat is very relaxing, the lyrics send a clear message and overall the song just flows together so well. Definitely worth at least one listen, even if you aren't a fan of other Gang Starr songs.
SNSD - Gee
OK, I lied, there's one more recent song on my list. This song just stands out in almost all categories for me; the beat is sick, the song has a wicked flow, and the chorus is really catchy. I also think the verses are really well-done, and overall I strongly recommend this song to any hiphop fan out there.