(Paying Subscribers, please keep scrolling at the bottom for five complete rare recordings of Freddie Webster.)
We have covered a tremendous amount of new ground in this series on Freddie Webster, who died before he turned 30 (1917-1947). The first six essays were entirely filled with discoveries about his life and career. In the seventh essay we began talking about his music, and we listened to a generous selection of his recorded legacy—twenty-one solos!—that took us from his debut in 1938 through 1942. Today you’ll hear ten more from 1943 to 1947, and then we will come to some conclusions.
Let’s begin this last installment with the most talked-about number in Webster’s repertory—his performance of Jerome Kern’s “Yesterdays,” which everyone agrees was a “showstopper”—that is, it got so much applause that it was hard to continue after that. Luckily, one of his performances of this with Jimmie Lunceford’s band was preserved on a radio broadcast in the Jubilee series, from probably June 1943, or possibly July. The arrangement was by Freddie himself, according to his obituary in the Pittsburgh Courier (see essay 6). But you may be surprised at what you hear. This is not a “jazz” arrangement in any usual sense, but instead is a written-out feature modeled after the classical cornet showpieces popularized by the soloists with John Philip Sousa’s band. In Webster’s piece, the dramatic beginning, the changes in tempo, and the flashy solo part are all in the tradition of, say, “The Debutante,” aka “Caprice Brillante,” written and performed by the famous Herbert L. Clarke. Here is Clarke’s recording from 1908:
Clarke retired in the early 1920s, but his recordings were well known—Louis Armstrong, for one, said he knew Clarke’s recordings, including this one in particular. And many other brass artists took up the tradition. For example, the Mexican trumpet virtuoso Rafael Méndez was very much active in the 1940s playing these kinds of pieces.
Here now is Webster on “Yesterdays” (There is a familiar quote at 0:30 but I can’t quite recall the name of it?)
A very flamboyant performance, and one can tell that this would have indeed been unique and memorable in the middle of a jazz concert. But does it reveal Webster to be a great jazz improviser? No, because clearly that was not the point of this tightly structured showpiece.
A note about Webster as a composer: He didn’t write much music that we know of during his short life, but as I just noted he arranged this “Yesterdays,” and presumably wrote out, or at least supervised the writing of, all of those complicated parts. I have also read that he wrote a tune called “Sepia,” never recorded. And in the previous essay, you heard his solo on “Reverse the Charges” with jazz singer-pianist Sonny Boy Williams. This was clearly a song meant to have popular potential, and it appears to have been the subject of a dispute between the two musicians. The September 1942 copyright application lists them both for the music, with Williams typed in first, and just Williams for the words, and Lewis Music Publishing Company as the copyright owner. Just a few months later, in May 1943, another application lists Webster as the first composer and Williams as the copyright owner. And the instrumental version, which we’ll hear below, lists only Webster on the 78 rpm label. The words aren’t sung of course, but usually the lyricist would have been credited anyway. There is more to this story, but overall it appears they were struggling over the credits. In any case, it never became a hit, although Etta Jones and Dakota Staton recorded it much later, in the early 1960s.
Moving along with his recordings, below is a swinging Webster solo from “On the Alamo” with Benny Carter’s band, a radio broadcast, undated but definitely from September or October 1943. (The complete recording, featuring Carter’s solo, is in the Bonus below.) Following that you’ll hear him on another broadcast, March 29, 1944, leading “Embraceable You,” in an arrangement that Sabby Lewis commissioned from Tadd Dameron for his band’s long N.Y.C. engagement. It’s likely that Webster recommended his old friend Dameron to Lewis, and Tadd wrote other arrangements, not preserved. Next, Webster solos on “Boston Bounce” with Sabby Lewis from the same broadcast (not to be confused with the more common studio recording of this piece from 1946, which has a muted solo by a different trumpeter). Here are those three solos:
We’re going to spend some time with his session from May 2, 1945 below. So let’s skip over for now that to finish this overview, starting with “Miss Rhapsody” (actually Viola Wells), “I Fell for You,” May 15, 1945. Next, from May 1946, you’ll hear the beginning and ending of “If You Could See Me Now,” a Dameron original, with Freddie leading Tadd’s “orchestra,” as it was called on the label. Then, from the same day, his solo on “You’re Not the Kind.” And finally, you’ll enjoy Webster’s last recorded solo, the bridge and last A section of “Perdido,” with Johnny Powell’s band in Cleveland in early 1947. I believe the 78 r.p.m. label said “Ready for Freddie,” indicating that it was dedicated to the returning “home town” artist, Webster. (The complete recording is in the Bonus below.) Here are all of the above:
Now we will study Freddie’s three solos from his most bebop-oriented record date, led by little-known tenor saxophonist Frank “Frankie” Socolow on May 2, 1945. (The unedited complete tracks are below for Paying Subscribers, as well as two other Webster recordings.) The rhythm section is Bud Powell (p), Leonard Gaskin (b), and Irv Kluger (dm). Socolow, born in 1923, was six years younger than Webster, and therefore was much more involved in the new bebop movement. This created some conflict at the start of the recording session, which bassist Gaskin described in the Teddy Reig biography:
I was on a [recording] date Teddy produced with Frankie Socolow which was total chaos. It was Frankie’s first date [as a leader] and the trumpeter Freddy [sic] Webster was on it…A controversy arose because Freddy wanted to play ballads to show off his tone, and Frankie wanted to do something rhythmic [that is, faster and swinging]. Teddy was the A & R man and somehow he had to deal with the situation. It took a lot of negotiating.
One result of the negotiation was that Reig and Socolow agreed to play one tune by Webster, “Reverse the Charges,” which we just discussed. Playing a tune that he knew well would help him to feel comfortable musically— and might potentially bring him more royalty income as well. They also recorded the ballads “Lover Man” and “September in the Rain.” But “…Rain” was performed at a faster tempo, likely at Socolow’s insistence and against Webster’s best interests. A fourth number was recorded but never released. It was yet another ballad, “Blue Fantasy.” There are several songs by that name—Artie Shaw had recorded one—but this was probably the one that the John Kirby group played, because Webster performed with them the previous year. But neither song by was generally known among musicians. So he probably attempted to teach it to the others, then they recorded one take, and the result was unsatisfactory.
In short, Webster was not ready to play bebop, and he knew it, or at least he knew that wasn’t his strength. It is intriguing to recall that in Essay 6 we learned that Freddie played a concert with Bud, Gaskin and Max Roach soon after this session, on May 12. Perhaps that was explicitly arranged for him to get more experience with bop. Or perhaps it was the other way around—maybe he or someone else thought that playing on this recording session would help him to get ready to play this style before an audience.
Let’s hear first his solo on “Reverse the Charges,” followed by “The Man I Love.” Let’s listen closely, and honestly, to his solos:
Can we be honest? At the very opening of that first solo, his sound, which is effective on a big band showpiece like “Yesterdays,” here comes across as loud and “blatty.” And melodically both solos are awkward—even the Dizzy Gillespie lick that he throws in at 0:20 seems out of place. Well, let’s keep listening. He takes a full chorus on “September in the Rain”:
Now, I have played this “September…” solo for over 200 music graduate students over about 20 years, and without exception they are always disappointed. In fact they are astounded that this is a person who has gone down in history as one of the great jazz trumpeters. The beginning of the solo is plodding and falls completely flat. Then at 0:12 he throws in the same Gillespie lick he used on “Reverse…,” but this time he follows it with a random run, exactly the kind of miscalculation that Miles talked about in the audio interview that you heard in the previous essay. The phrase leading into the bridge, 0:21 to 0:24, again falls flat. There is no suspense, no propulsion leading into the bridge.
But I know from experience that many people do not want to give up on the Webster legend. They listen to this solo with the specific agenda of proving that he was a bebop player. They make comments like “That riff sounds a little boppish, don’t you think?” Or, “I think Miles sounds a little like that.” Or, “Okay, it sounds a bit off, but overall it’s very good.” All of these statements show that the listener is trying too hard. Please pay attention to what is actually on the recordings—not what you wish was there. Can you honestly say that this is one of the best jazz trumpet solos you have ever heard??
On page 99 of Ira Gitler’s book Swing to Bop is a statement from trumpeter Benny Bailey (1925-2005), a native of Cleveland who was very devoted to Webster. This quote, below, has been misunderstood by a number of authors, who claim that Miles memorized a recorded solo by Webster. In fact, Bailey is not referring to any solo that Webster ever recorded—and there is no recording that fits his description. He is saying that Miles worked on his solo with Freddie before the recording date to get ideas, just as he did during the “Rubberlegs” date discussed in a previous essay. Bailey believed that Miles had memorized a solo that Webster showed him:
I happen to know for instance that on the recording of “Billie’s Bounce,” which Miles made with Charlie Parker [in November 1945], his solo was exactly the one Freddie played for this particular blues [that is, Freddie had a memorized blues solo that he used at gigs or in private]. Evidently Miles said he was nervous on the date and couldn’t think of anything to play, so he did Freddie’s solo note for note.
However, even with the limitations that I just listed, Bailey was still wrong, because we have the alternate takes, and Miles does not play the same solo “note for note” every time. He solos for two choruses on each of three takes—1, 3 and the issued take 5—and he plays three completely different improvisations. (Here is a link to all the takes on Spotify. Takes 2 and 4 broke down before Miles got to solo.) So it appears that he got some ideas from Webster, not a complete memorized solo. More important, nobody, not even Miles himself, ever thought that his playing on “Billie’s Bounce” was a highlight of his career. It’s largely characterized by the clumsy repetition of adjacent notes, as in C-D-C-D, which is simply a device to keep it moving. If Miles did get ideas for this from Webster, it’s only further proof that Webster had not mastered bop. Miles quickly outstripped Webster as a bebop player, and that’s when he began to teach Webster how to play bop, as we discussed.
So where did the idea come from that Webster was a leading bebop player? Well, if we’re being honest, the truth is that authors made it up from nowhere. Miles and Dizzy, and others, loved Freddie, not only as a player but as a person. So, many writers simply assumed, wrongly and without evidence, that Webster was an early bebop master—despite the fact that, as we saw last time, not one of his admirers said that he was a bebopper at all. In fact, one journalist even argued with me as follows: 1.“Miles and Dizzy both stated that they loved Webster.” OK, that is true. 2. But then the author made this absolutely false deduction: “Therefore, he must have been a great bebop player like them.” Sorry, that is false. 3. “But,” the argument continued, “his recordings do not show him to be a bebop player—in fact they show that he sounds very awkward the few times that he tries to play bop.” That is true, indeed. 4. This ridiculously illogical argument concludes, “Therefore, he must have in fact been a great bebopper, but the recordings fail to capture him at his best. He must have been in bad shape every single time that he recorded.” How ridiculous! Remember, he recorded more than 50 solos, over a period of 9 years! Are we really supposed to believe that none of this legacy can be trusted?
That line of thinking is completely wrong and makes no sense. The only sensible conclusion is that the reason you cannot find great recordings of Webster playing bebop is, quite simply, that he was not a bebopper, period! Miles and Dizzy loved him not for bebop, which he was just learning, but for his tone and for his personality. More generally, whenever there is recorded evidence—and in this case there is plenty—it is a completely unacceptable research practice to discount all of it because you “believe” the person played differently or better when he or she was not being recorded. In a very real sense, in music, what you hear is what you get! The sounds are what you must believe! As Lester Young said to my late friend François Postif in 1959, “Seeing is believing, and hearing is a bitch—that’s a sound!”
It’s interesting to note that Webster was just a month older than Gillespie—both were born in 1917. But Gillespie was one of the oldest people to get involved in modern jazz—along with Dameron and Monk, also born in 1917. Most musicians born that year became involved in the swing music of the 1930s and never moved on to bebop—and Freddie was one of those. You have now heard Webster solo on many swing recordings where he sounds excellent. To remind yourself, just go to “On the Alamo” above—nice! His recordings give a very clear picture of someone who is a strong swing player, but who did not fully grasp bop.
Without a doubt and beyond all dispute, Webster was admired by just about everyone in the early bop era. He was beloved as a person too, among musicians. But most people today know nothing of Webster because they haven’t sought out the recordings where he solos—and there are many of them—over fifty! He was influential primarily for overall trumpet technique and tone. Also, remember that things can make a big impression on us when we are young, and can sound vastly different if we hear them again years later. Webster’s recorded solos were hard to find before the CD era, so it’s fair to assume that in these old interviews, musicians were talking about his music entirely from their memories of 30, 40, even 50 years earlier. If they had heard the recordings I have shared with you, they very likely would have changed their statements. Dear reader, haven’t you ever had the experience of hearing something that you loved when you were young, and saying, “Hmm—it’s not as good as I remembered”? That is surely the case here.
And what about his swing playing? He was a strong swing trumpeter, but was he one of the greatest? Jan Evensmo, after studying all of the solos, wrote: “I do not find the soli that consistent and perfect as should be expected from a trumpeter that legendary.” And about “You’re Not the Kind,” which you heard above, he wrote, “I am really not impressed, it could even be considered overstepping the limits of good taste, being close to schmaltzy.” Gunther Schuller in his essential book The Swing Era (p.390), studied every studio recording of Webster (but not the radio broadcasts), and concluded that in general he “sounds directionless and unspecial, even inept.” Jazz historian Dan Morgenstern, a very reliable witness and someone who always tried to be positive, was asked to write about the two Minton’s recordings that you heard last time. But at that time it wasn’t known that this was Webster (later it was found that his name was written on the disc), so this made a good “blindfold test.” Dan wrote, “[He] is strongly affected by Frankie Newton (those descending phrases) and Lips [Page] (the half-valve stuff and clipped accents). He is also less assured and fluent than [Joe] Guy. {T]here are in jazz many capable, modestly gifted players whose names are not entered on the rolls of history. [He] is no giant, but he doesn’t do anybody any harm, as Eddie Condon used to say.”
By all accounts, Webster was most admired for his tone. But, some trumpeters have said to me, “I don’t even understand what’s so great about his tone? I don’t like it. It’s absolutely not a tone that would be acceptable today. In fact, if I played that way people might even laugh at me.” The answer is that it’s impossible for us today to hear his tone the way Miles and Dizzy did in 1944 and 1945. That’s eighty years ago! You cannot apply today’s standards to Webster’s sound. By the standards of their generation, in “live” performance, Webster sounded great, to them.
To conclude this series, which contains by far the most extensive research ever done on Freddie Webster, let’s repeat our conclusions from Essay 6: As a person, he was a warm, lovable man, a fancy dresser, someone who was fiercely anti-racist and carried a gun, and an artist who knew his value and asked for “star” treatment. He was also, at least during the winter of 1943-44, a troubled man who considered and once attempted suicide. But he recovered, and was fondly remembered by all who knew him.
As a musician, he was a superior swing trumpeter, somewhat in the vein of Roy Eldridge and Hot Lips Page, with a distinctive big, fat tone. During his last few years he was actively studying the new bebop language, partly with the help of Miles Davis, but he died before he was able to master it. His reputation was based largely on his tone and his vivacious personality, and of course on his bold swing style.
I hope you have enjoyed this series on Freddie Webster.
All the best,
Lewis
P.S. For tracking down “Perdido,” thank you to David Brent Johnson, host of an excellent jazz history radio program.
Dear Paying Subscribers,
I am always thankful for your support. Here are some more gifts for you. Above, you heard only Webster’s solos from these recordings. Now, you’ll hear the complete tracks. First, Benny Carter’s big band with Webster plays “On the Alamo,” from a radio broadcast in September or October 1943. The arrangement is by a young Frank Comstock. Webster enters at 1:04:
Next, here is “Perdido,” aka “Ready for Freddie,” by the Johnny Powell big band, a local legend in Cleveland, in early 1947. This one is tricky, because there are actually two trumpeters soloing. In my judgement, an unknown trumpeter (we have two names, but we don’t know which one it is) takes the first half of the chorus at 1:40. Webster’s big sound takes over at 2:02:
And finally, here is the complete session of May 2, 1945. The leader was tenor saxophonist Frank Socolow, along with Webster, Bud Powell (p), Leonard Gaskin (b), and Irv Kluger (dm). Powell is brilliant throughout, as always in this era—not only in solos but behind the others. It is believed that the tunes were recorded in the order that I’m giving them below. First, “The Man I Love”:
Next, “Reverse the Charges,” co-composed by Webster:
As I noted, “Bue Fantasy” was never released, so the last title is “September in the Rain”:
THANKS AGAIN!
All the best,
Lewis

Thinking back to some reading decades ago that I haven't tried to document I think I recall some people saying also about Clyde Hart that, although the records don't show it, he was an early bopper. My sense is that the records show he was a swing pianist who happened to be at a lot of the sessions where bop was being worked out.
I knew Frank Socolow (1923-1981); I met him and his wife Joanne not long before Frank's death of cancer at age 57. They were neighbors of mine in Riverdale (NW Bronx). Frank and Joanne spent their honeymoon on Artie Shaw's 1949 band bus. Both were lovely people, and Frank was for years a well-respected player on the NYC music scene. Also, both were dog lovers, and for years they sponsored an annual benefit jam session concert for animal welfare. Among the participants were David Allyn, Manny Albam, John Glasel, Johnny Carisi, Aaron Sachs, Ron Odrich, Marky Markowitz, and many others, myself included.