Early 90s - AA had so many easy partnership opportunities with fixed bonuses, it was easy to pile up miles without even trying. I was also flying a bunch of TW and they'd always have crazy stackable promotions - route bonuses, Amex bonuses, threshold bonuses, etc. The free tickets earned with their promotions were often valid to the continental U.S. plus Caribbean, so we'd typically use them for an island getaway.

The VDB game was super-predictable. My regular Friday afternoon trips home were a reliable $1000-1500 double-bump during peak travel weeks. They'd allow a 727 to be oversold by 40 people, issue 15-20 actual vouchers, and put everybody on the next 727 that, with all of the bumpees, was now also oversold by 30-40 people. Then they'd bump another 5 or 10 off of that flight and put everybody on the 10PM flight that was mostly empty, so upgrades were easy. When I was 24 and single, sitting at an ORD sportsbar drinking beer on the airline's dime was okay with me. VDBs funded pretty much all of my vacations (and that for much of my family) for the better part of a decade.

About 1982, Holiday Inn had their program going. 1 stay equals 1 point. During one or two months 1 stay equals 2 points. 60 points and receive 2 air tickets and one week at a Holiday Inn anywhere in the world. We flew to JNB, a week at very nice hotel in Sandton. Drove up to Sun City for a few days and capped the trip with two nights at Mala Mala. Haven't stayed at a Holiday Inn since 1984.

About 1992, Chart House Restaurants ran a promo. Visit all 60 restaurants and receive two round the world air tickets. Partners in Chart House thought one or two might do it. I was number eleven, but the first that actually dined in all 60. Others had cheated.....mostly lawyers.....using partnerships. Imagine such a scheme surviving more than one hour today. Haven't been to a Chart House since 1994.

Marriott had some sweet spots in their chart. This is from the 1989 chart.

Q8 - 140K Marriott points
8 night stay at any Marriott hotel worldwide (they had 170 at the time)
2 RT coach tickets anywhere in the world (I've noted a caveat of no coach on their partner Northwest)
Free 7 day rental car, full size
The award certs did not need to be used on the same itinerary.

Marriott owned two cruise ships for a time that were based in Greece. We used points for a free cruise of the Greek Islands.

The TWA reward chart was ridiculous. It kept me flying thru St Louis til the end. I remember an early promo: fly 5 flights and 5000 miles. Receive an award ticket in F for anywhere in the USA. We figured out a 5 segment routing from San Diego to NYC that came in at about 5030 miles for little over $200. We had a great weekend in NY with friends. They gave their two award tickets to her parents to fly to Alaska in F. We used ours to fly to Hawaii in F. The TWA awards also included free nights at Hilton International, a vastly superior chain to the domestic Hilton. We had some remarkable stays at hotels around the world.

I remember the Wendy's AirTran coupons on the drink cups. This was 2005. On a windy day the tossed away cups would accumulate in the back of the parking lot and I got a couple of free flights out of it. 34 cup coupons for a free one-way (or close to it).

In the very first days of Coke Rewards you could get Hilton points, no limit. Scored a bunch, asked friends to save their caps/codes. Limits on rewards/redemptions soon followed.

Back when SkyWest was operating as the Delta Connection in California with Metro III and Brasilia turboprops, it was easy to earn DL miles on short trips within the state. For example, a round trip flight between San Luis Obispo and San Diego via a connection both ways at LAX would earn 4000 miles or 1000 miles per segment SBP-LAX-SAN r/t.

As for redeeming miles, I remember when for a mere 100,000 CO OnePass miles one could fly round trip between Houston and Paris via Continental on the domestic legs and Air France on the transatlantic legs. And the AF legs were round trip on the Concorde.

We flew UA Paris<-->Athens round trip 5K miles round trip each in 1994! And bumped into one of our pilots at dinner!

Also, in the 90s, it was crazy fast to accrue miles and status as an Alaska MVP.
Using Alaska miles, we learned the hard way that "direct" is not the same as non-stop. Direct from SEA to Cabo included a stop at PDX!

Ha!! I lived in the UK in the early 1990s and knew people who participated in that. Even knew a couple people who actually got to take the free flights to New York, plus some others who got screwed. (Apparently tens of thousands of people got hosed and never saw their free flights.)

I read in a marketing industry magazine many years later how this one promotion vastly changed the perception of Hoover as a brand and altered the trajectory of the entire vacuum industry even beyond the UK. In the 80's, Hoover was practically a monopoly. By the 90's, there was serious visceral hate for this company and several new entrants ripping substantial market share away from them. (Dyson being one.)

I also saw a more-lighthearted piece about how secondhand stores and rummage sales were awash in cheap Hoover vacuums for years afterward. People bought hundreds of thousands of them just for this promo and a year later they were everywhere for 20 quid.

A lot of this kind of *Best* was also before the advent of the two-edged sword loyalty programs that rationalized, codified and mostly limited the favors by a "cultivated" CSR.

As part of this discussion, I want to add a blanket shout out to the United Concierges, followed by the 1K Room, followed by United's Room 3333 (shhhh!). Miracle workers, all. "Yes. No problem!" Chasing you down the corridor unlimited times with upgrades for no instruments, hotels for Wx, and the most miraculous - knitting together separate PNRs when one trip ran into the next and you were at the other end of the world. And concluding with: "...Thank you for flying with us!"

Those were the days. AA had their "AAngels" that could do just about anything and often did.

Nowadays, they still say "Thank you for flying with us" but it comes out more like "Thank us for flying you."

I don’t remember the exact year (late 80’s), in my late twenties I was upgraded to business from LGA to CLE because I had on a suit and tie.
she said, it’s nice to have someone young and well dressed in our business cabin

I'm gonna say that wouldn't be worth wearing a suit and tie to me.

Jay Leno had a great bit about 20 years ago regarding Delta slogans.

First, it was "Delta Is Ready When You Are". That's an airline I can get behind.
Then, "Delta, the Airline Run by Professionals". OK, I like.
Then, it was "We love to fly and it shows". Ah, this sounds like a nice airline.
Finally, "Delta gets you there". So that's all they're committing to now.

I redeemed a similar award in 1991 with IIRC two 3-night hotel certificates. It was an open jaw SFO to ATH and return from CAI with stopovers in Rome and Paris. Those were the days.

The best deal ever was the Continental Freedom Passport. Travel once per week for a year for less than $2000. You had to be 65. I met a guy who bought two of these so he could fly round trip each week. In 1988 he collected triple miles for all his trips.Jackpot!