Here are my recommendations for 25 essential CDs on which you can build your collection and develop your own likes and dislikes.  Click on the artist's name to read their Wikipedia entry, or click on the CD title to bring you to the CD on Amazon if you would like to hear samples of the tunes and see more information on the recording.

Picking 25 CDs to represent jazz is a foolish task and massively biased by my own tastes, which focus heavily on the 1950-1965 time period.  I am partial to Blue Note, and to the recordings engineered by Rudy Van Gelder (All About Jazz has a wonderful interview with Van Gelder).  The selections are in alphabetical order by artist, not time or favorite order, so listen to them all and have fun.  The first CD is my primary recommendation for that artist, and in many cases I couldn't resist giving you other terrific second and third choices as well.  Let me know what you think and give me some recommendations.

If you are looking for a great jazz DVD, try the 1960 classic Jazz on a Summer's Day, a very hip documentary from Newport '58 with some truly amazing performances by Anita O'Day and Jimmy Giuffre, among many others. For jazz history you can't beat the Ken Burns PBS Series Jazz which is on DVD, but is not without its detractors who are still quibbling about who was left out.  Another (much shorter) lovely jazz history DVD is A Great Day in Harlem, the story behind the classic Art Kane 1958 Esquire magazine cover photograph. 

Louis Armstrong:  25 Greatest Hot Fives and Sevens (1925-29).  Where modern jazz began in the mid-1920s. This is a “best of” disc that draws from a larger four CD box set of material from Louis’s groups during the 1920’s. Given the technology of the time, these are remarkable recordings and a great place to start. At the other end of Armstrong’s career (1961) is a remarkable duet album with Duke Ellington, The Great Summit.  The combined genius of these two consummate professionals in full maturity leaves me laughing out loud every time I listen to it. For even more fun, get the two disc set that includes not only the master takes, but also a second CD with full dialog between Louis, Duke, and Bob Thiele in the booth and the stops and starts of the session. If you close your eyes and listen you can hear the master takes fall into place through trial and error, a gas.  You can’t underestimate Armstrong’s impact on jazz nor his stature for over four decades.  Louis and Ella Fitzgerald combined forces to release several joint efforts, with the single CD Best of Ella Fitzgerald and Louis Armstrong (1956-57) a great place to start, or you can buy the complete 3 CD collection.  A remarkably soulful pair, Ella and Louis were magic together.  Ella’s remarkable instrument contrasted with Louis’s scratchy and impeccably timed delivery (and his great trumpet playing as well) is one of the great pairings in jazz history.

Count Basie:  I prefer the “Old Testament” Basie big band of the late 1930’s and early 1940’s to the “New Testament” big band of the early 1950’s (but they are both superb).  The Basie band was way ahead of its time, moving the idiom from swing/dance music to the more creative construct we think of today.  That band, plus a fair number of cool small session groups of the early 1950’s are captured on a great four CD set America’s #1 Band.  A close runner up is The Complete Decca Recordings, a 3 disc set recorded in 1937. It really swings too, but the overall sound quality is less satisfying.

Art Blakey and the Jazz Messengers:  Moanin’ (1958). It’s almost impossible to pick just one Messengers album, but here’s my best shot. Art Blakey is one of my favorite drummers, who mentored an entire generation of jazz musicians as they passed through the Jazz Messengers.  Other great Messengers albums include The Jazz Messengers (1956), Mosaic (1961) and Buhaina’s Delight (1961) among many others.  The recording engineer was Rudy Van Gelder, whose nuanced and sparkling recordings stand head and shoulders above his peers.

Sonny Clark: Cool Struttin’ (1958). Sonny on piano with arguably the best rhythm section in jazz - the incomparable Paul Chambers on bass and Philly Joe Jones on drums. Add Jackie McLean on alto sax and Art Farmer on trumpet and you get a classic. A Van Gelder recording. Other favorite Sonny Clark albums are Sonny’s Crib (1957) and Leapin’ and Lopin’ (1961).

John Coltrane:  Blue Trane (1957). Coltrane was one of the most influential tenor sax players (or musicians in general) in jazz history. One of the earlier, more traditional Coltrane recordings before he became more experimental, it is a classic, with the aforementioned Paul Chambers and Philly Joe Jones joined by Kenny Drew on piano.  Another Van Gelder gem. Other Coltrane classics include Giant Steps (1959), Ballads (1962), and the more avant garde A Love Supreme (1964).

Miles Davis: Kind of Blue (1959). Perhaps the greatest album in jazz history, it’s the one you should not be without. Miles asked piano genius Bill Evans to rejoin the quintet for this session, and focused the musicians on modes, or scales, rather than the more traditional chord progressions. The result was exquisite, an extraordinary collection of music. Miles' direction on Kind of Blue was influenced by the modal theory of George Russell, which he called the Lydian Chromatic Concept.  The four 1956  recordings of the early Davis quintet are also favorites of mine - Steamin’, Workin’, Cookin’, and Relaxin’.  The 1961 live recording of In Person - Friday and Saturday Nights at the Blackhawk with a "transition" group of Wynton Kelly, Hank Mobley, Paul Chambers, and Jimmy Cobb is outstanding.  The second longer term incarnation of the quintet with Herbie Hancock, Wayne Shorter, Ron Carter and (especially) Tony Williams is thrilling, with the pricey 8 disc Live at the Plugged Nickel (also available as a single "Highlights" CD) my favorite of that lineup.  Many folks are fans of his later fusion work, especially Bitches Brew, but he lost me later in his career.

Bill Evans: Evans is far and away the artist I connect with most strongly.  Sunday at the Village Vanguard (1961). Along with Kind of Blue, a must have CD. What is known as the “First Trio” with Paul Motian on drums and young genius Scott LaFaro on bass, they recorded this remarkable music live over two sets on a Sunday in June 1961. The other CD released from this set is more ballads, but almost as impressive - Waltz for Debby.  The full output of this remarkable day of live music including both discs has recently been remastered and released as The Complete Village Vanguard Recordings.  La Faro was killed in an auto accident driving from this session to their next gig, a tragic and premature end to a brilliant career and association with Evans. I’d strongly recommend Moonbeams (1962) as a second selection.  After LaFaro’s death Evans did not record for some time, but this album was the first with the so-called “Second Trio”, where Chuck Israels replaced LaFaro. A bit more introspective, it is a beautiful disc. I could fill the entire list of 25 with Evans recordings, he’s my favorite musician, so please check out several others.  The first two trio recordings, Everybody Digs Bill Evans (1958) the first CD with LaFaro, Portrait in Jazz are superb. Two excellent LPs are now released on one CD - Empathy (1962) and A Simple Matter of Conviction (1966).  And at the risk of overload, my favorite later Evans are Quintessence (1976) and I Will Say Goodbye (1977) where his playing takes on a more mature, wistful feel. And of course, he is featured on Miles Davis’ Kind of Blue.  A remarkable musician and brilliant man.

Ella Fitzgerald:  The Best of the Song Books (1956-64).  Producer Norman Granz guided Ella through a remarkable series of “songbooks”, where over almost a decade she recorded a series of 12 LPs dedicated to the songs of eight composers - Harold Allen, Irving Berlin, Duke Ellington, George and Ira Gershwin, Jerome Kern, Johnny Mercer, Cole Porter, and Rogers and Hart. This best of disc is a great way to sample the twelve CDs or full 16 CD box set of recorded material.  Looking for another Ella recording?  For a listen to early, smaller setting  Ella, check out Pure Ella (1950) with longtime accompanist Ellis Larkins. For the big band Ella try The Complete Ella in Berlin - Mack the Knife (1960).

Dexter Gordon: Go (1962). Gordon drives a bop groove as hard as anyone.  He left the U.S. for Europe only a few days after recording Go, where he found less racial discrimination and and a more hospitable jazz scene.  Another Van Gelder recording, the playing on this disc doesn’t let up. I keep coming back to this disc for my dose of hard bop. Other Dexter standouts include A Swinging Affair (1962), Our Man in Paris (1963), and One Flight Up (1964).

Grant Green: Idle Moments (1963). Grant Green was a wonderful, if somewhat overlooked guitarist.  The standout on this CD is the 15 minute title cut, which is an exquisite use of a lag tempo to invoke an idle summer day where the only time that matters is right now. I also really like Green Street (1961), Born to be Blue (1961), and Matador (1964).

Johnny Griffin: A Blowin’ Session (1957). Tenor greats Johnny Griffin and Hank Mobley were waiting on the street for producer Alfred Lion to pick them up and drive to Rudy Van Gelder’s New Jersey studio for this session when John Coltrane bumped into them.  When told of their plans, Coltrane asked if he could join the session, and what resulted was one of the classic tenor battles ever recorded.

Herbie Hancock:  Takin’ Off (1962). Hancock’s first album as leader, I think it is one of the easiest recordings for listening to how a melody and solo unfold. The playing is brilliant, but sparse and simple, making it a classic for younger players.  Empty Pockets is a killer tune.  Other Hancock classics include Empyrean Isles (1964) and Maiden Voyage (1965). You should probably own them as well...

We Three (1958). Haynes is one of the great jazz drummers of all time, and this trio CD with piano phenom Phineas Newborn and master bass player Paul Chambers is not widely known, but swings from top to bottom. Very cool CD.  Another great Haynes CD is Out of the Afternoon.  Roy is still playing today and is as tasty as ever. 

Joe Henderson: In ‘n Out (1964). In front of an unstoppable groove from Elvin Jones on drums, Richard Davis on bass, and McCoy Tyner on piano, Henderson and Kenny Dorham really stretch out. Also check out Page One and Our Thing for more Henderson and Dorham.

Billie Holiday: Songs for Distingue Lovers (1957). A classic from one of the great voices in jazz history.  Also available on a 2 CD set All or Nothing at All which includes all of the cuts from the two sessions in late 1956 and one in early 1957.  Billie enters your soul, as her late career, darker voice reflects her difficult life.  For the earlier Bille I'd recommend Lady Day and The Complete Decca Recordings.

Freddie Hubbard: Ready for Freddie (1962). My favorite from trumpeter Freddie Hubbard, he is joined by McCoy Tyner on piano, drum great Elvin Jones, and Wayne Shorter on tenor.  Other Hubbard favorites include Goin’ Up (1960) and Hub Tones (1962) with Herbie Hancock.

Lambert, Hendricks and Ross:  Sing a Song of Basie (1957). Dave Lambert, Jon Hendricks, and Annie Ross formed a truly remarkable vocal trio in the mid-1950s.  While some of their music had instrumental backing, for much of the music on this disc the trio use their voices to replicate the sound of jazz instruments improvising on classic Big Band tunes. Not to be missed.  For more LH&R, try The Hottest New Group in Jazz, which has one of the funniest cuts in jazz - Annie Ross in a brilliant version of "Twisted."

Charles Mingus: Mingus Ah Um (1959).  Mingus was one of the great innovators on bass, with a sound all his own. Don’t miss “Goodbye Pork Pie Hat” on this CD.  If you like Mingus, also check out Mingus, Mingus, Mingus, Mingus - it’s a little more experimental, but vintage Mingus.

Thelonious Monk: Straight, No Chaser (1966). Monk is hard to describe.  A brilliant piano player, he played with fingers splayed, and with great percussive effect.  Rhythm and syncopation was as important as melody, and he experimented with many unorthodox chords.  Charlie Rouse’s Tenor playing is phenomenal, all the more so considering the gaping holes left by Monk as he tip-toed though his sparse accents. The title tune is a must listen. Other great Monk classics include Brilliant Corners (1956), Monk’s Dream (1962), and Criss-Cross (1963).

Wynton Kelly with Wes Montgomery: Smokin’ at the Half Note (1965). An amazing live recording with some truly remarkable soloing by Wes Montgomery on guitar. For more phenomenal Wes Montgomery guitar check out The Incredible Guitar of Wes Montgomery (1960) and Boss Guitar (1963).  To hear Wes in his original Indianapolis bar band trio setting of guitar, organ and drums check out The Wes Montgomery Trio.

Oliver Nelson: Blues and the Abstract Truth (1961). You really must own this album. Right after Kind of Blue and Sunday at the Village Vanguard on the desert island list. Exquisite. Nelson and Eric Dolphy on reeds in front of Bill Evans (piano), Paul Chambers (bass) and Roy Haynes (drums). It doesn’t get any better than this. If you don’t like it on your first play, don’t despair, it often takes a few listens to get it.  For more Nelson/Dolphy listen to Straight Ahead (1961). A bit further out there, but brilliant.

Charlie Parker and Dizzy Gillespie: Diz ‘N Bird at Carnegie Hall (1947). The first five tracks are a remarkable quintet that featured Dizzy and Bird (Charlie Parker was known as “Bird”, short for “Yardbird”).  It’s a great recording to hear early Dizzy and a taste of Charlie Parker, who influenced an entire generation of tenor players. The balance of the CD is a big band featuring Dizzy, but not Bird. There has been much fuss lately about a newly discovered recording of Diz and Bird at Town Hall (1945) which is good, but in my opinion less interesting because of annoying emcee commentary and far less effective recording quality. It’s easy to forget that the Carnegie Hall album was recorded live in 1947, the quality is that good.

Sonny Rollins: Saxophone Colossus (1956). Rollins was known for a great tone, and a great sense of groove. This is one of his best albums, with Max Roach (drums), Tommy Flanagan (piano) and Doug Watkins (bass) a formidable rhythm section. Also check out Volume Two which features an amazing lineup - Horace Silver/Thelonius Monk, Paul Chambers, Art Blakey, and J.J. Johnson.

McCoy Tyner:  The Real McCoy (1967).   This album combines a great swing with the newer groove of the late 60s. One of the last of the classic jazz albums of the period, as the genre was overrun by rock.  The talent in this quartet is outstanding, with Joe Henderson, Ron Carter, and Elvin Jones (playing some killer drums) joining Tyner, who is at the top of his game on this CD.

Sarah Vaughan: Swingin’ Easy (1954). What a voice.  With this rare small trio backing instead of her more normal full orchestral backup (which can sound dated today), her voice takes on an even more musical quality. Two other great small group recordings are Sarah + 2 and Sarah Vaughan (with Clifford Brown).  The aforementioned Ella Fitzgerald and Billie Holiday, with Vaughan are arguably the three finest female singers jazz has known.