Almost all modern instruments of the brass wind family radiate sound through a single terminating bell. From the Middle Ages until the second half of the nineteenth century, lip-excited wind instruments with side holes were also in frequent use in both secular and sacred musical ensembles. The acoustical properties of labrasones with side holes, such as the cornetto, the serpent, the keyed bugle, and the ophicleide, resemble in may ways those of conventional brass instruments such as the trombone, but also have features which recall woodwind instruments like the oboe and saxophone. This paper presents some recent studies on the playability of labrasones with side holes, acknowledging the outstanding contributions of William J. Strong and his collaborators to the experimental study and modelling of both woodwind and brass instruments.