I cannot beat Connies, but my 1st ride was in Il-18. I remember the wing and the props fairly distinctly. Boy that thing smoked. I also took a ride in Tu-104 and remember the passage over the wing box with 3 tiny portholes. I paxed on Tu-134, Tu-154 (of course), and An-24. The last one performed an amazing cross-wind landing and rolled on 1 main wheel for a couple of seconds in heavy rainstorm in Harkiv, Ukraine. Back then I didn't know a thing about piloting, so this maneuver puzzled me for many years. Sadly, my family wasn't connected enough to hitch a ride on Tu-114.
In post-Soviet times, I flew Il-96-300 once to a freshly independent Uzbekistan. It already had the PS-90 engines - the last gasp of Soviet aviation industry. However, even high-bypass turbofans could not make competitive a ship with 4 crew on the flight deck.
My first ride in a little airplane was in a Skyhawk for a sightseeing trip over Lassen Volcanic Park in California. I flew the right seat and made a couple of tentative turns.