Checkrides are a part of life in a pilot's world. From your first checkride for your Private Pilot license to your most recent, they are for the most part pretty standard. Aborted takeoff, then some stalls and steep turns, maybe an unusual attitude. A coupled ILS approach to a missed approach and hold. A non-precision approach to a circle to land. Another takeoff, this time with an engine failure, followed by an ILS single engine to a landing. There can be some slight variances, but for the most part they're pretty predictable. Most of the time.
My Private Pilot checkride started out with me arriving an hour and a half late. Not my fault, the previous pilot got back late and I had to fly to another airport for the checkride. The examiner was fuming. We went out and did all the required maneuvers. I focused on the flying and not the lightning storm seated next to me. Finally he says "Give me a short field landing." So I did, picture perfect, in the last third of the runway. D'Oh! As we taxied in he said I had done fine (he'd calmed way down by now), and said about the short field landing, "Don't be afraid to go around if it isn't right." So I passed.
My first Part 135 (VFR) checkride was with Maddog Zimba in a Cessna 182 at my first job. He smoked constantly. He hopped in, lit up a Marlboro and said "Take me to Gardner's Island". I started looking at the map because I knew where Gardner's Island was, I just didn't know they had an airport. They didn't. He lets out a big sigh, grabs the map, "Give me that! It's right here!" he shouts, jabbing a big finger at the center of the island. We took off ("Finally! I didn't think you'd ever get going!") and flew across Long Island Sound. "Why are we at 7500 feet?!" he yells at me. I said it was so if the engine quits we can glide to shore. "Quits where?! What shore?" I said, well, it depends on the wind. If there's a headwind we would go a little farther... "Oh, you are so full of shit!" We descend to Gardner's Island and I enter an upwind because we are still high from our cross channel descent. "Christ almighty!! What the hell is this?! You're burning up all my gas!!" I land in the tall grass and he hops out, telling me to "stay here" while he lights up his fourth cigarette with his buddies up on the hill. When he gets back, he lights up Marlboro number five and says "Take me to the Devil's Hopyard." I start up and taxi back, do a soft field takeoff ("Worst damn takeoff I've ever seen") and fly back to Connecticut with my finger on the chart. The Devil's Hopyard is a private grass strip his friend owns and it isn't easy to find. I found it though, and landed ("Worst landing ever! Lucky to be alive!!"). He told me "Stay here. There's snakes everywhere" and went up for a smoke with his friend. Came back, lit up Marlboro number eight and we took off. At 200' he shoved the nose over and said "High enough! Low cloud deck. Take me home if you can. Which I doubt." I flew back following the roads and landed. He stormed off. I told Bruno our chief pilot about it and he said "Oh yeah. He always does that. If you can survive a flight with him, you can survive any passenger."
Flew a checkride at Northwest Airlink one night in a Saab 340 with check airman Jim Hadstate. We were up in Hibbing MN and it was snowing. We took off around midnight and leveled off at 7000' in the clouds. "Give me a steep turn to the left and right," he said. "Really? In the clouds?" He looked at me and asked "Do you want to come up here again on another day off and do this again?" Well, no, so I did two steep turns, and two stalls, in the clouds in icing conditions. We were in the process of negotiating our first union contract, so Jim had a lot to say about that. Talked non-stop about the contract while I flew the ILS, did a V1 engine failure on takeoff, then later a single engine circle to land in this snowstorm at around 2am. "You really need to focus on the Captain's pay. 500 above minimums. The per diem is important too. We need an industry, 100 above minimums, standard per diem rate. Ref plus ten. Minimums. And don't forget the duty time limitations!"
One night I met Lanny Riley at the hotel. We went out for dinner and I asked him if he wanted to do the oral exam at dinner, or later. He looked at me and asked "Dave, how long have you been flying the Saab?" "About six years now." "You really need an oral?" And that was the oral. Best ever.
April, 2016. I'm slated to take my checkride/type ride in the Metro IV with the FAA observing. Oh great, what fun. Also the Metro Program Manager showed up to observe too. Remember, the Metro is a very difficult airplane to fly, and the sim is worse. So we get through a 3 1/2 hour oral exam, then later climbed in to the sim. The air conditioning at FlightSafety was broken again, and in San Antonio it was HOT. Me, the examiner, the FAA and the Program Manager all squeezed into this sim with no AC. 3 1/2 hours later we are soaking wet with sweat, just about to shoot the final approach of the checkride when the sim overheats and crashes. We got out, stood around for ten minutes, then got back in, stinking like a high school gym locker room after a big game, and the sim managed to go in motion just long enough for us to complete the ride. Worst ride ever.
Have I ever failed a checkride? Nope, never. Not one. I think it was the fear of going home afterward and telling everyone I wasn't good enough that kept me from busting a ride. Fear of humiliation is a giant motivator. Huge.