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We study the optical $gri$ photometric variability of a sample of 190 quasars within the SDSS Stripe 82 region that have long-term photometric coverage during $\sim 1998-2020$ with SDSS, PanSTARRS-1, the Dark Energy Survey, and dedicated follow-up monitoring with Blanco 4m/DECam. With on average $\sim 200$ nightly epochs per quasar per filter band, we improve the parameter constraints from a Damped Random Walk (DRW) model fit to the light curves over previous studies with 10-15 yr baselines and $\lesssim 100$ epochs. We find that the average damping timescale $\tau_{\rm DRW}$ continues to rise with increased baseline, reaching a median value of $\sim 750$ days ($g$ band) in the rest-frame of these quasars using the 20-yr light curves. Some quasars may have gradual, long-term trends in their light curves, suggesting that either the DRW fit requires very long baselines to converge, or that the underlying variability is more complex than a single DRW process for these quasars. Using a subset of quasars with better-constrained $\tau_{\rm DRW}$ (less than 20\% of the baseline), we confirm a weak wavelength dependence of $\tau_{\rm DRW}\propto \lambda^{0.51\pm0.20}$. We further quantify optical variability of these quasars over days to decades timescales using structure function (SF) and power spectrum density (PSD) analyses. The SF and PSD measurements qualitatively confirm the measured (hundreds of days) damping timescales from the DRW fits. However, the ensemble PSD is steeper than that of a DRW on timescales less than $\sim$ a month for these luminous quasars, and this second break point correlates with the longer DRW damping timescale., Comment: 20 pages, 24 figures