They say beauty is in the eye of the beholder. Thankfully, aviation buffs have plenty of genuinely beautiful aircraft to admire. Consider the Supermarine Spitfire of WW2, which inspired Pilot Officer John Gillespie McGee to write of how he “slipped the surly bonds of earth / And danced the skies on laughter-silvered wings.” Or marvel at the raven-black, arrow-shaped form and features of the incredible SR-71 Blackbird, splitting the edge of space at Mach 3.3. The need to dance the skies has led to some of the most graceful machines ever built by humanity.

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However, they also say that form follows function, and the function of an aircraft can lead to some genuinely awkward forms. Specific missions call for strangely shaped wings, oddly proportioned fuselages, and overall shapes that sometimes are barely recognizable as airplanes. The planes on our list no doubt have their admirers, and some of them are excellent machines that excelled at what they were designed to do. But few people will go to the mat to defend them as beautiful.

The form factors of these planes range from odd, duck-shaped contraptions to planes that look like flying phone booths to cartoonishly bulging cargo planes. Some of these planes never made it out of the experimental testing phase, while others served for decades. Pilots have an old joke with a kernel of truth: any landing you walk away from is a good one. Conversely, any aircraft design that successfully takes to the skies could be considered good — but not necessarily beautiful. In approximately chronological order, here are ten of the worst-looking planes of all time.

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The AD Scout, built by the U.K.’s Air Department during the First World War, provides an excellent example of a plane’s mission dictating its form. Its role was to defend Britain from the unprecedented threat of Germany’s Zeppelins, the strategic bombers of their day. Most aircraft in this era of aerial warfare couldn’t travel long distances or carry enough munitions to represent a threat to distant cities, but the lighter-than-air Zeppelins possessed both the range and the payload to strike fear into distant populations. This threat wasn’t just theoretical either: in January of 1915, Zeppelin raids on the island of Britain commenced with the bombing of two British towns. For the first time in centuries, the British people were on the front lines of a war.

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To counter the threat, the British Admiralty’s Air Department engaged an aircraft designer and engineer named Harris Booth to design a plane whose sole mission was to hunt Zeppelins. To give pilots a better view of their prey, the Scout’s fuselage was mounted to the upper wing. This gave the AD Scout an ungainly appearance that looked like it might tip forward on landing, and indeed, a skid had to be attached ahead of the landing gear to prevent that very thing from happening.

If its appearance on the ground wasn’t graceful, things didn’t improve much in flight. The Scout was overweight and handled poorly. It also couldn’t handle the heavy Davis two-pounder gun it was originally intended to carry, necessitating a lighter and more standard gun to be fitted. While the plane was initially accepted for combat, it was soon discontinued and became a mere footnote in the Great War.

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If it looks like a duck but roars like an airplane, which is it, exactly? The Curtiss-Goupil Duck exists to answer that question. It’s an airplane, of course, but according to some, it’s one of the ugliest aircraft in history. Its existence arose from a dispute over patents. In 1906, the Wright Brothers were awarded a patent for lateral control of a powered aircraft using wing warping, which twisted the shape of their airplane’s wings as a method of steering. One of their competitors, Glenn Curtiss, hoped to bypass their patent by using ailerons. This led to a patent dispute with the Wrights, who claimed a monopoly on powered flight that required royalties from anyone building aircraft.

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To counter the Wright Brothers’ claim, Curtiss needed to prove that lateral control predated the Wrights’ first flight. He discovered the work of French engineer Alexandre Goupil, who had designed a bird-like monoplane glider in 1883 that demonstrated stability during unpowered test flights. Goupil’s design included small horizontal surfaces that could function either as elevators or ailerons. Goupil had intended to add an engine to his design, but that never bore fruit.

Curtiss built an aircraft based on Goupil’s patent drawings, replacing the 1,000 pound steam engine that Goupil envisioned with a lighter 100 horsepower engine. On January 19, 1917, the Curtiss-Goupil Duck completed both straight and circular flights, demonstrating that lateral control existed before the Wright Brothers’ patent. However, Curtiss’s patent dispute with the Wrights was resolved later that year when the United States government convinced Orville Wright to relinquish the patent for wartime aircraft production. The Duck never went into mass production.

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The Blackburn Blackburd was as ungainly as the spelling of its name. Designed to be as simple as possible to build, it wound up looking like something a child might make from a box. Like several of the planes on this list, it arose out of the necessities of war. The Blackburd was a torpedo bomber, intended to replace the Sopwith Cuckoo (also built by Blackburn), which had gone into large-scale production near the end of the First World War. The British Admiralty intended for the Blackburd to be capable of operating from carriers.

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The Blackburn Blackburd was a single-engine torpedo bomber designed as a three-bay biplane powered by a 350 horsepower Rolls-Royce engine. Its top speed was 95 mph, although this dropped to 90.5 mph when carrying a 1,400 pound torpedo. The Blackburd’s most visually striking feature was its rectangular side profile, which looked like a single box from just behind the engine bay all the way to the tail. One observer at the time described the aircraft as looking like it was “undoubtedly built for use and not for ornament.” This ungainly design resulted, at least in part, from a specification that required the Blackburd to be fast and cheap to produce.

The aircraft also featured a unique wing design where all four wings employed ailerons which doubled as flaps to reduce take-off and landing speeds, though testing revealed this reduced take-off capabilities. This was just one of several issues with the Blackburd. For instance, the plane needed to jettison its landing wheels to drop its torpedo, relying on steel skids for landing afterward. Flight testing also determined the Blackburd to be front-heavy and its rudder too small. Ultimately, only three prototypes were produced.

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The Pterodactyls were a series of flying wing designs built in the 1920s to demonstrate that tailless aircraft could be viable. Though none served in combat, they were precursors to modern flying wing designs. British Royal Air Force Captain Geoffrey T.R. Hill was behind the unusual design. His goal was to build a safer plane in light of crashes that killed dozens of Royal Air Force pilots. Hill’s theory held that a tailless flying wing would never go out of control due to pilot error.

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Captain Hill began designing what would become the Pterodactyl in 1923. By December 1924, it was ready for testing as a glider. HIll took it to a remote rural area of the South Downs in the colorfully named Devilsrest Bottom. This glider had wings that swept noticeably backward, a very unusual feature for the early 1920s, with moveable extensions to the wingtips that functioned as elevators or ailerons, depending on how they were operated. With a catapult assist and a slight headwind, the glider needed only ten yards to get airborne. Once Hill had proven the airworthiness of his design, the Air Ministry stepped in to provide an engine, engaging the assistance of Westland Aircraft.

This led to a series of prototypes initially known as the “Hill Tailless Monoplane,” but eventually, the aircraft became called Pterodactyls. The bodies were built of lightweight balsa wood, and a pusher propeller was mounted on the rear of the short, two-seater fuselage. (The final prototype had a front engine and propeller.) The plane’s stall speed was very low, and if the pilot let go of the stick, it would return to center, and the Pterodactyl would level off. This made the aircraft very stable and safe to fly.

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The XF-85 Goblin’s cartoonishly stubby appearance resulted from the need to fit into the bomb bay of long-range bombers, giving the bombers a built-in fighter escort. This symbiotic relationship earned the Goblin the nickname of parasite fighter. Its absurdly short fuselage and tiny wings were designed to nestle into the bomb bay of a B-36 Peacemaker, although flight tests were conducted in 1948 with B-29 Superfortress bombers. Its baby-jet appearance might be described as cute rather than ugly, but there’s no way it could be called graceful.

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Had the Goblin gone into production, a trapeze would have lowered it from the bomb bay of the B-36 mothership when enemy fighters approached. After dispatching the enemy, the Goblin would catch the trapeze to be raised back into the B-36. It would have had a decent chance at completing the defensive part of its mission since it could reach speeds of 650 mph. It sported four .50-caliber machine guns and was said to be easy to fly. 

However, flight tests revealed that it was difficult for pilots to catch the trapeze at the end of their defensive mission. As a result, half of its test flights ended with emergency landings on the ground. Plus, changes in aerial warfare led to the Goblin becoming one of several US fighter jet prototypes that never took to the skies as production models. Specifically, the viability of aerial refueling had extended the range of fighter jets so that conventional jets could escort long-range bombers. 

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The X-13 Vertijet was an early attempt at a vertical takeoff and landing (VTOL) jet fighter, but it was designed to take off on its tail, resulting in a strange, foreshortened appearance. Its mission resulted from Cold War concerns about vulnerable airfields in an era of nuclear threats. The U.S. military wanted an aircraft capable of operating without conventional runways, leading Ryan Aircraft Corporation to develop this experimental fighter. The concept originated from discussions among engineers about whether Ryan’s existing FR-1 Fireball could take off vertically, and soon morphed into an actual engineering project.

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Development began with the U.S. Navy before transferring to the Air Force in 1954. The X-13 was a compact delta-wing fighter with distinctive winglets and fixed landing gear. The aircraft used a sophisticated control system featuring a vectorable exhaust nozzle and wingtip air thrusters for vertical landing operations. It was tested in conventional flight before the first vertical flight test on May 28, 1956. The X-13 operated from a specialized trailer tilted vertically, allowing the aircraft to hang from a cable by its nose hook. For takeoff, the pilot gently increased the throttle until the jet lifted off the cable before accelerating vertically and then transitioning to horizontal flight.

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When landing, the Vertijet was supposed to approach the recovery trailer and hook onto a cable, but this proved to be the most challenging and impractical part of the operation. Pilots had to approach the recovery trailer blind, with ground observers guiding them to the recovery trailer by radio. Even though the pilot’s seat pivoted 45 degrees during landings and takeoffs, visibility was severely limited. The Vertijet was never deployed, but its thrust vectoring technology later became essential in combat aircraft like the legendary Harrier jump jet.

In the modern era, Russia’s Ilyushin Design Bureau mostly builds civilian and military transport aircraft, but in Soviet times, it was a leading combat aircraft manufacturer. One of its odder-looking products was the Il-40. This plane, whose nose resembled a double-barreled shotgun muzzle, was intended to perform a close air support mission for ground troops, similar to the legendary A-10 Warthog of the U.S. Air Force. The Il-40’s development grew out of a realization in the early years of the jet age that the new generation of jet fighters were excellent at high speeds but not very efficient at the slow, lingering flight needed for close air support.

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To serve that role, the Il-40 offered low-speed maneuverability and excellent armor to protect the two-man crew from ground fire. The first engine configuration for the Il-40 had conventional air intakes on the sides of the fuselage. For its attack role, the plane featured four bomb bays and additional racks under the wings for bombs, rockets, or external fuel tanks. Six 23-millimeter autocannons in the nose gave the Il-40 an additional, devastating punch.

Unfortunately for Ilyushin, the first time a test pilot fired those cannons at a ground target, the fiery gasses from the cannons blinded him and got sucked into the engine intakes, causing a flameout. The pilot was able to recover and save the jet. Ilyushin first tried a series of muzzle covers with little success and eventually extended the engine air intakes all the way forward to the nose, giving the plane its strange snout. Despite the fixes, the Il-40 never went into mass production.

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Perhaps comparing the Transavia AirTruk to a flying phone booth is unnecessarily harsh, even though its short, vertical fuselage looks oddly out of place with wings on it. The AirTruk is another example of form following function, and it functioned as a cropduster. These kinds of aircraft often suffer corrosion of the tail end of the fuselage due to the chemicals they spray, so the AirTruk’s designer, Luigi Pellarini, dispensed with the tail section altogether. What was left of the fuselage was essentially a tank for agricultural chemicals with a propeller on the front. The cockpit rested on top of the tank, giving the plane its oddly stubby, vertical appearance, like something from a Pixar cartoon.

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The AirTruk is a biplane with a small lower wing above the fixed rear landing gear. Twin tail booms extend from the upper wing, spaced widely enough for a truck to back up to the fuselage for reloading the AirTruk so it can get back to work quickly. With the pilot’s high viewpoint, he or she could easily keep an eye on the chemical dispersion over the fields behind the plane. Dual outlet doors on the bottom of the fuselage offered excellent dispersal patterns. Racks below the lower wing could be used to drop supplies in remote locations — very useful in Australia, where the plane was developed and used.

While the AirTruk is not a fast aircraft, especially while hauling a load, it gives good feedback to the pilot and is easy to land due to its heavy-duty landing gear and the pilot’s unobstructed view from way up high. Production numbers weren’t huge, but fittingly for an Australian plane, it made a memorable appearance in “Mad Max Beyond Thunderdome.”

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The next plane on our list has its fans, but that doesn’t change the fact that its wings look like they were put on backward, making the Grumman X-29 one of the strangest jets ever designed. Its development was a collaboration between NASA, the U.S. Air Force, and the Defense Advanced Research Projects Agency (DARPA) to demonstrate several advanced aviation technologies. It served as a test bed for forward-swept wings, which provided exceptional maneuverability and speed.

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This maneuverability came at the price of stability, and the X-29 would have been difficult or impossible for an unaided pilot to fly. To counter this, the X-29 featured a bank of three flight computers offering fly-by-wire control, which adjusted the flight control surfaces at far higher speeds than could be achieved by hand. When the X-29 first took flight in December 1984, fly-by-wire was still a relatively new technology.

Other design features of the X-29 were cutting-edge for the mid-1980s, including its lightweight composite construction, variable-camber wing surfaces, and a thin supercritical airfoil, which is a wing shape designed to reduce drag. The X-29 was always intended to be a test bed for new technologies and not a serial production model, so only two were built, and they were retired after very successful careers.

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If you search the Internet for “pregnant guppy,” you may be more likely to get results describing the care of expectant tropical fish than an airplane. Nevertheless, there was a plane by that name, and it looked strange but served an important purpose. The Pregnant Guppy gave birth (so to speak) to a family of oversized cargo aircraft, but its historical importance is overshadowed by its swollen, cartoon-like appearance. Nevertheless, it did its job of transporting rocket segments very well.

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The Pregnant Guppy was a Boeing B-377 Stratocruiser modified by a company called Aero Spaceline Industries (ASI) to have a hugely expanded fuselage with a 20-foot-high cargo bay capable of transporting rocket parts and other bulky cargo to Cape Canaveral, Florida. This saved NASA from sending parts manufactured in Western states on a slow journey through the Panama Canal. 

The Pregnant Guppy became the predecessor of a line of supersized cargo planes. A larger version of the design with an even larger cargo hold became known as the Super Guppy. Finally, the Super Guppy Turbine (SGT) debuted with more powerful turboprop engines and a more oversized cargo floor. Four SGTs were built, and they were operated by Airbus Industries after being purchased from ASI. 

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