100 Years of Route 66, and the Top 5 Cars to Drive It In

<p>Alex and Randy, fresh off our recent gathering and film screening of  the forthcoming documentary series <a href="https://www.mainstreetofamerica.com/" target="_blank" rel="noopener"><em>Route 66: The Main Street of America</em></a> in Flagstaff, Arizona, discuss Randy&#39;s father-daughter trip from Riverside to Flagstaff in his red Chrysler 300B; learning the Chuck Berry version of <em>Get Your Kicks on Route 66</em> backward and forward; swimming against the stream on the notoriously east-to-west road; the first post-prohibition liquor license in Chicago; the captivating documentary and the great, historic Orpheum Theater in which we got to see it; giving cars a reason to live; the temptation of the vintage motel and gas station business; love for the desert Googie diner; a brief &quot;stroad&quot; explainer; teaching kids patience and flexibility on the road; and that most elusive and necessary part of any good road trip: time.</p><p>They move on to a game of picking their top five ideal cars to do the whole route in, along the way discussing aesthetic over speed; candidates from a stakebed farm truck to a Duesenberg; if one could make the drive appropriately in a non-American car; whether a convertible is really a good idea; a Swiss tourist who had Randy pegged within seconds; and specific instances in which roll-up windows prove important.</p><p>What are your top five rides for the Mother Road?</p><p><strong>Follow along! Links for the listings discussed in this episode:</strong></p><p>12:55 <a href="https://bringatrailer.com/2026/10/08/route-66-bat-gathering-at-the-orpheum-theater-in-flagstaff-arizona/">Route 66 BaT Gathering at the Orpheum Theater in Flagstaff, Arizona</a></p><p>35:05  <a href="https://bringatrailer.com/listing/1970-ford-mustang-boss-302-79/">347-Powered 1970 Ford Mustang Boss 302 4-Speed</a></p><p>35:42  <a href="https://bringatrailer.com/listing/1970-ford-mustang-boss-302/">Lot 1: 1970 Ford Mustang Boss 302</a></p><p>38:25 <a href="https://bringatrailer.com/ford/f-series-1953-1956/">Ford F-Series 1953-1956</a> model page</p><p>41:26  <a href="https://bringatrailer.com/listing/1926-duesenberg-model-a-opera-coupe/">1926 Duesenberg Model A Opera Coupe</a></p><p>45:53  <a href="https://bringatrailer.com/volkswagen/beetle-1958-1979/">Volkswagen Beetle (1958-1979)</a> model page</p><p>47:53  <a href="https://bringatrailer.com/search/?s=1957+nomad">1957 Chevrolet Nomads</a> on BaT</p><p>48:46  <a href="https://bringatrailer.com/listi