It’ll take more than 5 albums to be a ‘true, up-to-date hip hop fan’, I’m afraid.
Albums that are pretty well essential to hip hop culture, and changed hip hop:
Rakim & Eric B - Paid In Full (Rakim basically created the style of rap all MCs use today)
Wu-Tang Clan - 36 Chambers (often named as the best hip hop album ever)
Nas - Illmatic (it’s New York, in 10 songs - absolute classic)
Dr Dre - The Chronic (these beats were made more than 10 years ago, and they still sound modern - warrants the ‘ahead of its time’ tag more than any other album)
Tupac - Me Against the World (political, passionate, compelling - at his best, Pac was incredible)
Notorious B.I.G - Ready to Die (the best album from the widely considered King of New York)
Run DMC - (I can’t remember the album names, but they single-handedly took hip hop out of the underground)
Public Enemy - It Takes A Nation Of Millions to Hold Us Back (intensly political and innovative)
A Tribe Called Quest - (can’t remember the album, but they are also considered pioneers of hip hop)
All of these albums are reasonably modern (ie. the oldest out of these was released in 1989, I think), and they’re the albums that brought hip hop to the forefront of music. I’ll name the artists that, once you’ve learnt about the basics of hip hop, you should definitely check out:
Az - Very underrated; an excellent lyricist. Check out ‘Aziatic’.
Jay Z - Listen to ‘Reasonable Doubt’ and ‘The Blueprint’. Smooth flow, and nice beats.
50 Cent - His old work was much better than his new album. Buy ‘Guess Who’s Back?’ or download ‘Power of a Dollar’.
Big Pun - Incredible flow and multi-syllabic rhyme scheme. Constantly switched between Spanish and English rapping.
Big L - Was killed before he had a chance to properly shine. Another excellent lyricist (get ‘Lifestyles of the Poor and Dangerous’).
Canibus - His albums aren’t good, on the whole, but he is a stunning battle lyricist, with a lot of genuine intelligence.
Dilated Peoples - Lovely beats, good lyrics.
Dead Prez - Highly political - buy ‘Let’s Get Free’.
De La Soul - Old Skool tracks.
Del - Get ‘Deltron 3030’. Basically, just a great rapper.
GZA - Member of the Wu Tang Clan. ‘Liquid Swords’ is hailed as a classic.
Outkast - Get ‘aquemimi’. Dirty South brilliance.
MOP - Grimey, with incredible beats. They represent New York.
Method Man - Another Wu Tang member, with a wicked flow and delivery.
Naughty By Nature - Old Skool hip hop.
Snoop Dogg - ‘Doggystyle’ is also hailed as a West Coast classic.
Slick Rick - Get ‘The Adventures of Slick Rick’. Often touted as the best hip hop storyteller ever.
Artists that are less well known, but that you should check out anyway, once you’ve waded through that lot:
Talib Kweli - Very deep rapper
Boom Bap Project - Very underground; very good.
Gangstarr - Stunning beats from DJ Premier, and a good rapper in Guru.
Jedi Mind Tricks - Fast, dark beats and incredible flows. I’m a big fan of JMT.
Kool G Rap - Another pioneer of hip hop. Was pretty much the first rapper to use multi-syllabic rhyme schemes.
Saigon - Currently in jail, but has amazing beats, an amazing flow and clever lines. (‘They say love is pain/ So would it be unconditional love if I put a hot slug in your brain?’)
Inspectah Deck - Another Wu Tang member. One of my favourite rappers for flow and delivery.
D Block - Consisting of Sheek and Jae Hood. Some quality tracks.
CL Smooth & Pete Rock - Old skool. Pete Rock is one of my favourite producers - his beats are stunning, and CL Smooth has awesome mic precense.
Aesop Rock - Very strange, but if you can understand him, his words are so poetic, metaphorical and complicated that he’s above the level of a rapper.
Demigodz - Consisting of Apathy, Celph Titled (both of whom you should hear seperately) and others. Great punchlines and beats.
Benefit - Great punches and storytelling
Binary Star - For rapping on a deeper level
DMX - Passionate rapping - he has a great mic precense.
Mobb Deep - Tight duo. Listen to ‘Shook Ones’, which was in 8 Mile, the movie, at the beginning.
Mad Skillz - Underrated battle rapper
Pharaohe Monch - Very original flow.
Redman - New York rapper that everyone seems to love
Rass Kass - Underrated battle rapper, who occasionally delves deeply into politics and society
X-Ecutioners - Taking it back to the days of scratching
That should keep you occupied for a little while