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Boeing, although it produced many larger narrowbodies, never designed its own regional jet; the only regional jet it ever produced was the DC-9 (from 1997 through 2006, in the DC-9-80 and DC-9-90 series), a (McDonnell) Douglas aircraft which Boeing inherited from Long Beach through a corporate merger.

Why didn't Boeing design and build its own regional jet earlier, to compete with the DC-9?

Boeing did have a small regional jet called the Boeing 727. This plane was designed to operate at smaller airports, with independence from ground facilities as a selling feature. The best example is that the 727 had built-in stairs in the rear underbelly of the aircraft. This could be opened in flight until some hijacker known as DB Cooper jumped out to make his escape.

The 727-100C could have a combination of 54 passengers and four cargo pallets of freight or up to 94 passengers in a mixed class with no freight.

Until it ended production at 1,832 aircraft, the 727 was the most popular passenger jet ever sold. Since that time, the most popular plane ever sold was the Boeing 737, which could have as few as 85 passengers with the 737-100.

Boeing met a definite need for airlines since it sold so many aircraft. A better question might be what could McDonnell-Douglas have done to meet airline needs and still be a viable competitor.

Well it did have one in the form of the ‘slugs’ - the earlier 737 classic aircraft. They sold outrageously well along with the 727s to fill regional or national routes.

And let’s not forget the airline business was considerably different than it is today in the form of structure and operations so what we consider a ‘regional’ aircraft is very different to what it was back then.

It really wasn’t until the 1990s with deregulation in full force and changes to the labor structure of the airlines going over to the ‘hub and spoke’ approach to travel, which facilitated the rise of the regional carriers and the intro of the fast and efficient 50-60 passenger regional jets. I suspect back in the ‘golden age’ of air travel pre deregulation and oil embargo, when 747s were a status symbol and iconic of the glamour of jet setting, there just would not have been a market, an interest, or both, in a large enough setting to justify investing in a jet that small.

The 737 is basically Boeing's regional jet, but ended up growing into something larger to meet customer demand.

The DC-9 was introduced in 1965 and had variants seating from 90 to 135 in a single class.

The 737 was introduced in 1968. Competition like the DC-9 was already taking over this market. The 737-100 was designed to seat 103-118 in a single class, right in the middle of the DC-9 market. But only 30 of these were built, mostly for Lufthansa. Customers wanted something larger, so the 737-200 was introduced, seating 115 to 130 in a single class. This covers the upper range of the DC-9 family, and over 1,000 of these were built, surpassing the DC-9. These variants were even powered by some of the same variants of the Pratt & Whitney JT8D that the DC-9 used.

The 737-500 was the Classic version that was designed to replace the 737-200, and almost 400 of these were built. The 737-600 was the Next Generation version to replace the 737-500, but only 69 were built. The 737 had grown to optimally carry more passengers. Boeing produced what began as the McDonnell Douglas MD-95 under the Boeing 717 name, but production ended amid slow sales. When the market for this size of plane picked up again, Boeing decided not to compete with companies such as Bombardier and Embraer in the regional jet market, as that would probably require a completely new design.