“What a Wonderful World” – Louis Armstrong

Chances are, you’re already quite familiar with this song. Louis Armstrong⁠⁠—known by some as Satchelmouth or simply Satchmo for his gravelly voice⁠⁠—is one of, if not the single most well known jazz singer and trumpet player ever. “What a Wonderful World” itself needs little introduction; like many others on this list, it is infectiously joyful, and has never failed to put a smile on my face. The instrumental is laid-back and perfectly matches the rest of the song, which depicts little more than an introspective walk. Despite its simple premise, the description of so many nice “little” things in the world is so well crafted, and Armstrong’s vocals are so sincere, that it would be difficult to make a song that is more exceedingly positive than this one without it coming off as preachy. Though this track in particular doesn’t feature his trumpet playing (and it’s absolutely worth listening to Armstrong’s other music, which is equally as iconic), “What a Wonderful World” is a quintessential song, both in jazz and in general.

“Take the ‘A’ Train” – Duke Ellington

Duke Ellington is an instantly recognizable name in the jazz scene, with him and his orchestra having written many of the standards of the genre. “Take the ‘A’ Train” is one of those standards, written by the less well-known pianist Billy Strayhorn, which features a blaring horn section and a catchy melody typical of songs recorded by Ellington. Short and sweet, the tune is one that personifies the spirit of joy and relative simplicity found in much of the other “big band” style jazz being made in the 1930s and 1940s. There are rich harmonies found in every section of the band, and they all meld together to create an even richer song overall. What puts the specific rendition on this list, rather than any of Ellington’s other recordings, is the vocal segment: Betty Roche singing over the band’s chorus-like back-up vocals is a treat. There is a reason why so many songs from this time are standards, as the catchiness and carefree nature of this piece, like many others, is simply infectious⁠⁠.

“Take Five” – Dave Brubeck

Dave Brubeck’s 1959 album Time Out is entirely about weird time signatures in jazz, and “Take Five” is no different. Most songs, regardless of genre, have a “four-four” time signature, meaning that there are four beats per a grouping of notes called a measure. “Take Five” entirely falls apart if you do that, because it is in “five-four” time, meaning there are five beats per measure. While a simple, smooth piece, the song is extremely catchy, and uniquely so because of its odd time. The track is a vessel not for its iconic sax lick, though, but for the drum solo that starts two minutes in and lasts for another two. It is a great solo, one that is fairly simple on the face of it, but ends up as an incredible feat of subtlety that draws the listener in as it continues on, accompanied only by the continuing piano. While it might take you out of your comfort zone after the saxophone drops out, the experience is so enticing as a whole that I can’t recommend it enough.

“Moanin’” – Charles Mingus

Out of all of the songs listed here, this one will be the hardest for anybody not into jazz to get into. It is chaotic, utilizing “group improvisation,” and goes on for a full nine minutes. By all accounts, Charles Mingus’ “Moanin’” should not be as successful of a piece of music as it is, but I find myself on the edge of my seat for the whole length of the song. It is unified, in part, by an incredible baritone saxophone line, with a lick that most sax players at Liberty would be glad to play for you. The reason why it stays interesting across three lengthy solos and only two other melodic ideas in the piece is because it varies the texture constantly. You never know when a new instrument is going to enter the fray, and yet there is never a time where that extra sound doesn’t feel completely welcome. I can’t recommend this song enough to those who enjoyed the rest of this list⁠⁠—while it is a completely different style of jazz from everything else here, it is well worth the listen if you can make sense of it.

“Mack the Knife” – Ella Fitzgerald

Jazz is an incredibly fun genre, and Ella Fitzgerald is the epitome of fun jazz. This recording in particular, immortalized in Fitzgerald’s album Live in Berlin, is incredibly fun due in part to her forgetting the lyrics after only a few choruses. Instead of the song being about a serial killer⁠⁠—and, yes, “Mack the Knife” is genuinely about a serial killer⁠⁠—Fitzgerald improvises lyrics regarding other people who’ve sang it, including both an incredible impression of Louis Armstrong and a number of lines regarding the “wreck” that she made of the song. Despite the clear flaw in the song, I think it’s a better showing of Fitzgerald’s particular strengths than anything else. Between the perfectly performing backing band and Fitzgerald’s sense of humor as she comes up with lyrics on the spot, this is a must-listen for anyone who enjoys music. After all, it should never be about perfection: Fitzgerald showed perfectly that sometimes getting things wrong can be even better than getting it right.