The following are the 27 guests of In Lieu of Fun who have appeared on the show at least five times, ordered by frequency of appearance and first episode. See also the full list of guests.

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Guest Count Episodes
Tim Miller (@Timodc)
Writer, author, journalist; former political director of RVAT 		19 47, 96, 125, 155, 202, 224, 273, 300, 316, 370, 390, 461, 496, 500.1, 536, 601, 640, 655, 673
Sarah Longwell (@SarahLongwell25)
Publisher of The Bulwark, founder of Republican Voters Against Trump 2020 		18 31, 147, 180, 189, 208, 220, 262, 286, 300, 320, 332, 339, 382, 399, 514, 546, 562, 646
Jonathan Rauch (@jon_rauch)
Senior Fellow at Brookings Institution; contributing writer at The Atlantic 		16 17, 73, 106, 206, 209, 230, 259, 271, 298, 319, 345, 403, 438, 473, 572, 608
Mike Chase (@TheMikeChase)
Criminal defense attorney, author, and maintainer of @CrimeADay 		11 3, 112, 126, 216, 276, 394, 441, 476, 517, 555, 597
Virginia Heffernan (@page88)
Journalist, critic, author; WIRED contributor; host of "This is Critical" podcast 		11 13, 67, 137, 216, 225, 377, 440, 493, 511, 589, 658
Peter Strzok (@petestrzok)
FBI and Army veteran; author 		11 195, 264, 341, 422, 471, 500.3, 544, 563, 617, 643, 649
Jack Balkin (@jackbalkin)
Constitutional law professor, and Director of Yale ISP 		10 7, 63, 145, 197, 291, 334, 524, 567, 670, 672
Scott Shapiro (@scottjshapiro)
Professor of Law & Philosophy at Yale; jurisprude 		9 10, 25, 148, 182, 220, 259, 281, 340, 377
Mike Pesca (@pescami)
Host of "The Gist" daily podcast; NPR contributor, editor 		9 13, 80, 229, 322, 507, 570, 587, 609, 674
Leah Litman (@LeahLitman)
Law professor, constitutional law & federal courts; co-host of "Strict Scrutiny" podcast 		9 39, 81, 95, 102, 105, 203, 416, 590, 654
Jordan Ellenberg (@JSEllenberg)
Mathematics professor, number theorist and algebraic geometer; author 		8 7, 243, 352, 418, 532, 574, 682, 683
Dan Drezner (@dandrezner)
Professor at the Fletcher School of Tufts University; author 		8 10, 21, 131, 164, 218, 316, 431, 595
Nate Persily (@persily)
Law professor, Co-Director of Stanford Cyber Policy Center, Healthy Elections Project 		8 11, 125, 132, 173, 311, 380, 485, 569
Alan Rozenshtein (@ARozenshtein)
Law professor, contributing editor at Lawfare; former Justice Department lawyer 		8 12, 45, 161, 185, 223, 276, 622, 666
David Priess (@DavidPriess)
Author, speaker, writer; COO at Lawfare; former CIA 		8 101, 181, 227, 276, 415, 527, 564, 659
Alex Stamos (@alexstamos)
Director of the Stanford Internet Observatory and former CISO of Facebook 		6 2, 11, 68, 158, 599, 679
Orin Kerr (@orinkerr)
Lawyer and law professor specializing in criminal procedure and computer crime law 		6 5, 25, 330, 411, 542, 672
Paul Rosenzweig (@RosenzweigP)
Senior Fellow at R Street; homeland security consultant 		6 62, 158, 320, 529, 556, 608
Kathleen Belew (@kathleen_belew)
Historian of white supremacist movements, at the University of Chicago 		6 85, 126, 201, 286, 287, 538
Molly Jong-Fast (@MollyJongFast)
Writer at The Atlantic & Vogue; co-host of the New Abnormal podcast 		5 26, 159, 200, 402, 457
Ada Palmer (@Ada_Palmer)
Historian, SF/Fantasy author, and composer 		5 32, 98, 354, 424, 500.5
Shane Harris (@shaneharris)
Covers intelligence and national security for Washington Post; host of "Chatter" podcast 		5 50, 314, 397, 554, 682
Reginald Dwayne Betts (@dwaynebetts)
Poet; Guggenheim, NEA, and MacArthur Fellow; winner of National Magazine Award 		5 56, 327, 475, 483, 526
Matthew Miller (@matthewamiller)
Former Director of the Office of Public Affairs for the Department of Justice 		5 76, 124, 125, 217, 332
Marty Lederman (@marty_lederman)
Law professor at Georgetown University, formerly a Department of Justice official 		5 84, 86, 95, 104, 105
Steve Vladeck (@steve_vladeck)
Law professor; federal courts, constitutional law, national security, military justice 		5 86, 114, 237, 284, 416
Alicia Wanless (@lageneralista)
Ph.D. researcher studying propaganda and human behaviour 		5 543, 585, 596, 630, 681