On the Smaller jets the Learjet 35 and the Falcon 20 had chutes.
M.E.
As did the 1211 Jet Commander and some IAI 1123 Commodore Jet. The Commodore Jet was the first version of the 1124 Westwind series.
To use the drag chute most effectively you had to brief it's use before landing. We tried to have the drag chute deploy as soon as possible at touch down. With enough experience we could deploy the drag chute just before we touched down where it would fully inflate just as we touched down.
One problem with new co-pilots was that they expected to feel the drag of the chute the second they pulled the handle. So when the order was given to deploy the chute, they would pull the handle out, then when they didn't feel any instant deceleration they would shove the handle back in and pull it out again.
Only one problem with this, pushing the handle back in was how the chute was jettisoned. So if people were watching, they would see the chute stream out from the tail and then just detach from the aircraft and fall on the runway. Sometimes the ATC tower controllers were not amused when this occurred.
This could be embarrassing, to say the least.